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href="https://ca.wikipedia.org/wiki/S%C3%ADntesi_total" title="Síntesi total – Catalan" lang="ca" hreflang="ca" data-title="Síntesi total" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Tot%C3%A1ln%C3%AD_synt%C3%A9za" title="Totální syntéza – Czech" lang="cs" hreflang="cs" data-title="Totální syntéza" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Totalsyntese" title="Totalsyntese – Danish" lang="da" hreflang="da" data-title="Totalsyntese" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Totalsynthese" title="Totalsynthese – German" lang="de" hreflang="de" data-title="Totalsynthese" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/T%C3%A4iss%C3%BCntees" title="Täissüntees – Estonian" lang="et" hreflang="et" data-title="Täissüntees" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9F%CE%BB%CE%B9%CE%BA%CE%AE_%CF%83%CF%8D%CE%BD%CE%B8%CE%B5%CF%83%CE%B7_(%CF%87%CE%B7%CE%BC%CE%B5%CE%AF%CE%B1)" title="Ολική σύνθεση (χημεία) – Greek" lang="el" hreflang="el" data-title="Ολική σύνθεση (χημεία)" data-language-autonym="Ελληνικά" data-language-local-name="Greek" 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</div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Complete chemical synthesis of a complex molecule</div> <p class="mw-empty-elt"> </p><p><b>Total synthesis</b>, a specialized area within <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, focuses on constructing complex organic compounds, especially those found in nature, using laboratory methods.<sup id="cite_ref-nature_1-0" class="reference"><a href="#cite_note-nature-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicolaou1_2-0" class="reference"><a href="#cite_note-Nicolaou1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicolaou2_3-0" class="reference"><a href="#cite_note-Nicolaou2-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicolaou3_4-0" class="reference"><a href="#cite_note-Nicolaou3-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It often involves synthesizing <a href="/wiki/Natural_product" title="Natural product">natural products</a> from basic, commercially available starting materials. Total synthesis targets can also be <a href="/wiki/Organometallic" class="mw-redirect" title="Organometallic">organometallic</a> or <a href="/wiki/Inorganic" class="mw-redirect" title="Inorganic">inorganic</a>.<sup id="cite_ref-Inorganic_synth_5-0" class="reference"><a href="#cite_note-Inorganic_synth-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RBW1963_6-0" class="reference"><a href="#cite_note-RBW1963-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> While total synthesis aims for complete construction from simple starting materials, modifying or partially synthesizing these compounds is known as <a href="/wiki/Semisynthesis" title="Semisynthesis">semisynthesis</a>. </p><p>Natural product synthesis serves as a critical tool across various scientific fields. In organic chemistry, it tests new synthetic methods, validating and advancing innovative approaches. In medicinal chemistry, natural product synthesis is essential for creating bioactive compounds, driving progress in drug discovery and therapeutic development. Similarly, in <a href="/wiki/Chemical_biology" title="Chemical biology">chemical biology</a>, it provides research tools for studying biological systems and processes. Additionally, synthesis aids natural product research by helping confirm and elucidate the structures of newly isolated compounds. </p><p>The field of natural product synthesis has progressed remarkably since the early 19th century, with improvements in synthetic techniques, analytical methods, and an evolving understanding of chemical reactivity.<sup id="cite_ref-armaly_7-0" class="reference"><a href="#cite_note-armaly-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Today, modern synthetic approaches often combine traditional organic methods, biocatalysis, and chemoenzymatic strategies to achieve efficient and complex syntheses, broadening the scope and applicability of synthetic processes. </p><p>Key components of natural product synthesis include <a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">retrosynthetic analysis</a>, which involves planning synthetic routes by working backward from the target molecule to design the most effective construction pathway. Stereochemical control is crucial to ensure the correct three-dimensional arrangement of atoms, critical for the molecule's functionality. Reaction optimization enhances yield, selectivity, and efficiency, making synthetic steps more practical. Finally, scale-up considerations allow researchers to adapt lab-scale syntheses for larger production, expanding the accessibility of synthesized products. This evolving field continues to fuel advancements in drug development, materials science, and our understanding of the diversity in natural compounds.<sup id="cite_ref-Fay_2023_8-0" class="reference"><a href="#cite_note-Fay_2023-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Scope_and_definitions">Scope and definitions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Total_synthesis&action=edit&section=1" title="Edit section: Scope and definitions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are numerous classes of natural products for which total synthesis is applied to. These include (but are not limited to): <a href="/wiki/Terpenes" class="mw-redirect" title="Terpenes">terpenes</a>, <a href="/wiki/Alkaloids" class="mw-redirect" title="Alkaloids">alkaloids</a>, <a href="/wiki/Polyketides" class="mw-redirect" title="Polyketides">polyketides</a> and <a href="/wiki/Polyethers" class="mw-redirect" title="Polyethers">polyethers</a>.<sup id="cite_ref-Natural_Products_9-0" class="reference"><a href="#cite_note-Natural_Products-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Total synthesis targets are sometimes referred to by their organismal origin such as plant, marine, and fungal. The term total synthesis is less frequently but still accurately applied to the synthesis of natural <a href="/wiki/Polypeptide" class="mw-redirect" title="Polypeptide">polypeptides</a> and <a href="/wiki/Polynucleotide" title="Polynucleotide">polynucleotides</a>. The peptide hormones <a href="/wiki/Oxytocin" title="Oxytocin">oxytocin</a> and <a href="/wiki/Vasopressin" title="Vasopressin">vasopressin</a> were isolated and their total syntheses first reported in 1954.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is not uncommon for natural product targets to feature multiple structural components of several natural product classes. </p> <div class="mw-heading mw-heading2"><h2 id="Aims">Aims</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Total_synthesis&action=edit&section=2" title="Edit section: Aims"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although untrue from an historical perspective (see the <a href="/wiki/Cortisone#History" title="Cortisone">history of the steroid, cortisone</a>), total synthesis in the modern age has largely been an academic endeavor (in terms of manpower applied to problems). Industrial chemical needs often differ from academic focuses. Typically, commercial entities may pick up particular avenues of total synthesis efforts and expend considerable resources on particular <a href="/wiki/Natural_product" title="Natural product">natural product</a> targets, especially if <a href="/wiki/Semi-synthesis" class="mw-redirect" title="Semi-synthesis">semi-synthesis</a> can be applied to complex, natural product-derived <a href="/wiki/Drugs" class="mw-redirect" title="Drugs">drugs</a>. Even so, for decades<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> there has been a continuing discussion regarding the value of total synthesis as an academic enterprise.<sup id="cite_ref-Nicolaou_prospective_12-0" class="reference"><a href="#cite_note-Nicolaou_prospective-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> While there are some outliers, the general opinions are that total synthesis has changed in recent decades, will continue to change, and will remain an integral part of chemical research.<sup id="cite_ref-Baran_-_Here_to_stay_15-0" class="reference"><a href="#cite_note-Baran_-_Here_to_stay-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-In_the_Pipeline_(1)_17-0" class="reference"><a href="#cite_note-In_the_Pipeline_(1)-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Within these changes, there has been increasing focus on improving the practicality and marketability of total synthesis methods. The <a href="/wiki/Phil_S._Baran" title="Phil S. Baran">Phil S. Baran</a> group at <a href="/wiki/Scripps_Research_Institute" class="mw-redirect" title="Scripps Research Institute">Scripps</a>, a notable pioneer of practical synthesis have endeavored to create scalable and high efficiency syntheses that would have more immediate uses outside of academia.<sup id="cite_ref-Baran_18-0" class="reference"><a href="#cite_note-Baran-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JOC_Time_economy_19-0" class="reference"><a href="#cite_note-JOC_Time_economy-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Total_synthesis&action=edit&section=3" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Expert_needed plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/40px-Ambox_important.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/60px-Ambox_important.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/b4/Ambox_important.svg/80px-Ambox_important.svg.png 2x" data-file-width="40" data-file-height="40" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs attention from an expert in chemistry</b>. The specific problem is: <b>The provided examples are poor, narrow in scope, and incomplete. This section would greatly benefit from a rewrite and expansion by experts in the field.</b><span class="hide-when-compact"> <a href="/wiki/Wikipedia:WikiProject_Chemistry" title="Wikipedia:WikiProject Chemistry">WikiProject Chemistry</a> may be able to help recruit an expert.</span> <span class="date-container"><i>(<span class="date">June 2021</span>)</i></span></div></td></tr></tbody></table> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:VitaminB12_retrosynthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/VitaminB12_retrosynthesis.svg/300px-VitaminB12_retrosynthesis.svg.png" decoding="async" width="300" height="400" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/VitaminB12_retrosynthesis.svg/450px-VitaminB12_retrosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/VitaminB12_retrosynthesis.svg/600px-VitaminB12_retrosynthesis.svg.png 2x" data-file-width="734" data-file-height="978" /></a><figcaption><b><a href="/wiki/Vitamin_B12_total_synthesis" title="Vitamin B12 total synthesis">Vitamin B<sub>12</sub> total synthesis</a>: <a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthetic analysis</a></b> of the Woodward–Eschenmoser total synthesis that was reported in two variants by these groups in 1972. The work involved more than 100 PhD trainees and postdoctoral fellows from 19 different countries. The <a href="/wiki/Retrosynthesis" class="mw-redirect" title="Retrosynthesis">retrosynthesis</a> presents the disassembly of the target vitamin in a manner that makes chemical sense for its eventual forward construction. The target, Vitamin B<sub>12</sub> (<b>I</b>), is envisioned being prepared by the simple addition of its tail, which had earlier been shown to be feasible. The needed precursor, <a href="/w/index.php?title=Cobyric_acid&action=edit&redlink=1" class="new" title="Cobyric acid (page does not exist)">cobyric acid</a> (<b>II</b>), then becomes the target and constitutes the "<a href="/wiki/Corrin" title="Corrin">corrin</a> core" of the vitamin, and its preparation was envisaged to be possible via two pieces, a "western" part composed of the A and D rings (<b>III</b>) and an "eastern" part composed of the B and C rings (<b>IV</b>). The restrosynthetic analysis then envisions the starting materials required to make these two complex parts, the yet complex molecules <b>V</b>–<b>VIII</b>.</figcaption></figure> <p>Friedrich <a href="/wiki/W%C3%B6hler_synthesis" title="Wöhler synthesis">Wöhler</a> discovered that an organic substance, <a href="/wiki/Urea" title="Urea">urea</a>, could be produced from inorganic starting materials in 1828. That was an important conceptual milestone in chemistry by being the first example of a synthesis of a substance that had been known only as a byproduct of living processes.<sup id="cite_ref-Nicolaou1_2-1" class="reference"><a href="#cite_note-Nicolaou1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Wöhler obtained <a href="/wiki/Urea" title="Urea">urea</a> by treating <a href="/wiki/Silver_cyanate" title="Silver cyanate">silver cyanate</a> with <a href="/wiki/Ammonium_chloride" title="Ammonium chloride">ammonium chloride</a>, a simple, one-step synthesis: </p> <dl><dd>AgNCO + NH<sub>4</sub>Cl → (NH<sub>2</sub>)<sub>2</sub>CO + AgCl</dd></dl> <p><a href="/wiki/Camphor" title="Camphor">Camphor</a> was a scarce and expensive natural product with a worldwide demand.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers"><span title="The time period mentioned near this tag is ambiguous. (March 2017)">when?</span></a></i>]</sup> Haller and Blanc synthesized it from camphor acid;<sup id="cite_ref-Nicolaou1_2-2" class="reference"><a href="#cite_note-Nicolaou1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> however, the precursor, camphoric acid, had an unknown structure. When Finnish chemist Gustav Komppa synthesized camphoric acid from <a href="/w/index.php?title=Diethyl_oxalate&action=edit&redlink=1" class="new" title="Diethyl oxalate (page does not exist)">diethyl oxalate</a> and <a href="/w/index.php?title=3,3-dimethylpentanoic_acid&action=edit&redlink=1" class="new" title="3,3-dimethylpentanoic acid (page does not exist)">3,3-dimethylpentanoic acid</a> in 1904, the structure of the precursors allowed contemporary chemists to infer the complicated ring structure of camphor. Shortly thereafter,<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers"><span title="The time period mentioned near this tag is ambiguous. (March 2017)">when?</span></a></i>]</sup> <a href="/wiki/William_Perkin" class="mw-redirect" title="William Perkin">William Perkin</a> published another synthesis of camphor.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Writing_better_articles#Stay_on_topic" title="Wikipedia:Writing better articles"><span title="The material near this tag may contain information that is not relevant to the article's main topic. (March 2017)">relevant?</span></a></i>]</sup> The work on the total chemical synthesis of camphor allowed Komppa to begin industrial production of the compound, in <a href="/wiki/Tainionkoski" class="mw-redirect" title="Tainionkoski">Tainionkoski</a>, <a href="/wiki/Finland" title="Finland">Finland</a>, in 1907. </p><p>The American chemist <a href="/wiki/Robert_Burns_Woodward" title="Robert Burns Woodward">Robert Burns Woodward</a> was a pre-eminent figure in developing total syntheses of complex organic molecules, some of his targets being <a href="/wiki/Cholesterol_total_synthesis" title="Cholesterol total synthesis">cholesterol</a>, <a href="/wiki/Cortisone" title="Cortisone">cortisone</a>, <a href="/wiki/Strychnine_total_synthesis" title="Strychnine total synthesis">strychnine</a>, <a href="/wiki/Lysergic_acid" title="Lysergic acid">lysergic acid</a>, <a href="/wiki/Reserpine" title="Reserpine">reserpine</a>, <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a>, <a href="/wiki/Colchicine" title="Colchicine">colchicine</a>, <a href="/wiki/Vitamin_B12_total_synthesis" title="Vitamin B12 total synthesis">vitamin B<sub>12</sub></a>, and <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandin F-2a</a>.<sup id="cite_ref-Nicolaou1_2-3" class="reference"><a href="#cite_note-Nicolaou1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Vincent_du_Vigneaud" title="Vincent du Vigneaud">Vincent du Vigneaud</a> was awarded the 1955 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> for the total synthesis of the natural polypeptide <a href="/wiki/Oxytocin" title="Oxytocin">oxytocin</a> and <a href="/wiki/Vasopressin" title="Vasopressin">vasopressin</a>, which reported in 1954 with the citation "for his work on biochemically important sulphur compounds, especially for the first synthesis of a polypeptide hormone."<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Another gifted chemist is <a href="/wiki/Elias_James_Corey" title="Elias James Corey">Elias James Corey</a>, who won the <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> in 1990 for lifetime achievement in total synthesis and for the development of <a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">retrosynthetic analysis</a>. </p> <div class="mw-heading mw-heading2"><h2 id="List_of_notable_total_syntheses">List of notable total syntheses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Total_synthesis&action=edit&section=4" title="Edit section: List of notable total syntheses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Quinine_total_synthesis" title="Quinine total synthesis">Quinine total synthesis</a><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nicolaou1_2-4" class="reference"><a href="#cite_note-Nicolaou1-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> First synthesized by Robert Burns Woodward and William von Eggers Doering in 1944, this achievement was significant due to quinine's importance as an antimalarial drug.</li> <li><a href="/wiki/Strychnine_total_synthesis" title="Strychnine total synthesis">Strychnine total synthesis</a> First synthesized by Robert Burns Woodward in 1954, this synthesis was a landmark achievement due to the molecule's structural complexity.</li> <li><a href="/wiki/Morphine_total_synthesis" class="mw-redirect" title="Morphine total synthesis">Morphine</a>: First synthesized by Marshall D. Gates in 1952, with subsequent more efficient syntheses developed by other chemists, including Toshiaki Fukuyama in 2017.</li> <li><a href="/wiki/Cholesterol_total_synthesis" title="Cholesterol total synthesis">Cholesterol total synthesis</a><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Synthesized by Robert Burns Woodward in 1951, this was a significant achievement in steroid synthesis.</li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a>: Another notable steroid synthesis by Robert Burns Woodward in 1951.</li> <li><a href="/wiki/Lysergic_acid" title="Lysergic acid">Lysergic acid</a>: Synthesized by Robert Burns Woodward in 1954, this was an important precursor to LSD.</li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a>: Completed by Robert Burns Woodward in 1956, this synthesis was notable for its complexity and the molecule's importance as an antihypertensive drug.</li> <li><a href="/wiki/Chlorophyll" title="Chlorophyll">Chlorophyll</a>: Synthesized by Robert Burns Woodward in 1960, this achievement was significant due to chlorophyll's crucial role in photosynthesis.</li> <li><a href="/wiki/Colchicine" title="Colchicine">Colchicine</a>: Another notable synthesis by Robert Burns Woodward, completed in 1963.</li> <li>Prostaglandin F-2a: Synthesized by E.J. Corey in 1969, this was an important achievement in the synthesis of prostaglandins.</li> <li><a href="/wiki/Vitamin_B12_total_synthesis" title="Vitamin B12 total synthesis">Vitamin B<sub>12</sub> total synthesis</a><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Completed by Robert Burns Woodward and his team in 1972, this synthesis is considered one of the most complex ever achieved, involving over 100 steps.</li> <li><a href="/wiki/Paclitaxel_total_synthesis" title="Paclitaxel total synthesis">Paclitaxel (Taxol) total synthesis</a>: First synthesized by Robert A. Holton in 1994, and later by <a href="/wiki/K._C._Nicolaou" title="K. C. Nicolaou">K. C. Nicolaou</a> in 1995, this anticancer drug's synthesis was a major breakthrough in medicinal chemistry.</li> <li><a href="/wiki/Brefeldin_A" title="Brefeldin A">Brefeldin A</a>: Synthesized by S. Raghavan in 2017, this complex macrolide has potential as an anticancer agent.</li> <li><a href="/wiki/Ryanodine" title="Ryanodine">Ryanodine</a>: Synthesized by Sarah E. Reisman in 2017, this complex diterpenoid has important biological activity.</li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Total_synthesis&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-nature-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-nature_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20141220143334/http://www.nature.com/subjects/total-synthesis">"Definition: Total synthesis"</a>. Nature Publishing Group. Archived from <a rel="nofollow" class="external text" href="http://www.nature.com/subjects/total-synthesis">the original</a> on 2014-12-20<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-08-22</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Definition%3A+Total+synthesis&rft.pub=Nature+Publishing+Group&rft_id=http%3A%2F%2Fwww.nature.com%2Fsubjects%2Ftotal-synthesis&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATotal+synthesis" class="Z3988"></span></span> </li> <li id="cite_note-Nicolaou1-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Nicolaou1_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Nicolaou1_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Nicolaou1_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Nicolaou1_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Nicolaou1_2-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNicolaouVourloumisWinssingerBaran2000" class="citation journal cs1"><a href="/wiki/K._C._Nicolaou" title="K. 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title="Bioretrosynthesis">Bioretrosynthesis</a></li> <li><a href="/wiki/Biosynthesis" title="Biosynthesis">Biosynthesis</a></li> <li><a href="/wiki/Chemosynthesis_(nanotechnology)" title="Chemosynthesis (nanotechnology)">Chemosynthesis</a></li> <li><a href="/wiki/Convergent_synthesis" title="Convergent synthesis">Convergent synthesis</a></li> <li><a href="/wiki/Custom_peptide_synthesis" title="Custom peptide synthesis">Custom peptide synthesis</a></li> <li><a href="/wiki/Direct_process" title="Direct process">Direct process</a></li> <li><a href="/wiki/Divergent_synthesis" title="Divergent synthesis">Divergent synthesis</a></li> <li><a href="/wiki/Electrosynthesis" title="Electrosynthesis">Electrosynthesis</a></li> <li><a href="/wiki/Enantioselective_synthesis" title="Enantioselective synthesis">Enantioselective synthesis</a></li> <li><a href="/wiki/Fully_automated_synthesis" class="mw-redirect" title="Fully automated synthesis">Fully automated synthesis</a></li> <li><a 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title="Solvothermal synthesis">Solvothermal synthesis</a></li> <li><a class="mw-selflink selflink">Total synthesis</a></li> <li><a href="/wiki/Volume_combustion_synthesis" title="Volume combustion synthesis">Volume combustion synthesis</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span><b><a href="/wiki/Category:Chemical_synthesis" title="Category:Chemical synthesis">Category</a></b></li> <li><span 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srcset="//upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/23px-Symbol_portal_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/31px-Symbol_portal_class.svg.png 2x" data-file-width="180" data-file-height="185" /></a></span><b><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Portal</a></b></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Branches_of_chemistry" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link 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title="Raman spectroscopy">Raman</a></li> <li><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-Vis</a></li> <li><a href="/wiki/Nuclear_magnetic_resonance_spectroscopy" title="Nuclear magnetic resonance spectroscopy">NMR</a></li></ul></li> <li><a href="/wiki/Mass_spectrometry" title="Mass spectrometry">Mass spectrometry</a> <ul><li><a href="/wiki/Electron_ionization" title="Electron ionization">EI</a></li> <li><a href="/wiki/Inductively_coupled_plasma_mass_spectrometry" title="Inductively coupled plasma mass spectrometry">ICP</a></li> <li><a href="/wiki/Matrix-assisted_laser_desorption/ionization" title="Matrix-assisted laser desorption/ionization">MALDI</a></li></ul></li> <li><a href="/wiki/Separation_process" title="Separation process">Separation process</a></li> <li><a href="/wiki/Chromatography" title="Chromatography">Chromatography</a> <ul><li><a href="/wiki/Gas_chromatography" title="Gas chromatography">GC</a></li> <li><a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">HPLC</a></li></ul></li> <li><a href="/wiki/Crystallography" title="Crystallography">Crystallography</a></li> <li><a href="/wiki/Characterization_(materials_science)" title="Characterization (materials science)">Characterization</a></li> <li><a href="/wiki/Titration" title="Titration">Titration</a></li> <li><a href="/wiki/Wet_chemistry" title="Wet chemistry">Wet chemistry</a></li> <li><a href="/wiki/Calorimetry" title="Calorimetry">Calorimetry</a></li> <li><a href="/wiki/Elemental_analysis" title="Elemental analysis">Elemental analysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Theoretical_chemistry" title="Theoretical chemistry">Theoretical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Quantum_chemistry" title="Quantum chemistry">Quantum chemistry</a></li> <li><a href="/wiki/Computational_chemistry" title="Computational chemistry">Computational chemistry</a> <ul><li><a href="/wiki/Mathematical_chemistry" title="Mathematical chemistry">Mathematical chemistry</a></li></ul></li> <li><a href="/wiki/Molecular_modelling" title="Molecular modelling">Molecular modelling</a></li> <li><a href="/wiki/Molecular_mechanics" title="Molecular mechanics">Molecular mechanics</a></li> <li><a href="/wiki/Molecular_dynamics" title="Molecular dynamics">Molecular dynamics</a></li> <li><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular geometry</a> <ul><li><a href="/wiki/VSEPR_theory" title="VSEPR theory">VSEPR theory</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Physical_chemistry" title="Physical chemistry">Physical</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Electrochemistry" title="Electrochemistry">Electrochemistry</a> <ul><li><a href="/wiki/Spectroelectrochemistry" title="Spectroelectrochemistry">Spectroelectrochemistry</a></li> <li><a href="/wiki/Photoelectrochemistry" title="Photoelectrochemistry">Photoelectrochemistry</a></li></ul></li> <li><a href="/wiki/Thermochemistry" title="Thermochemistry">Thermochemistry</a></li> <li><a href="/wiki/Chemical_thermodynamics" title="Chemical thermodynamics">Chemical thermodynamics</a></li> <li><a href="/wiki/Surface_science" title="Surface science">Surface science</a></li> <li><a href="/wiki/Interface_and_colloid_science" title="Interface and colloid science">Interface and colloid science</a> <ul><li><a href="/wiki/Micromeritics" title="Micromeritics">Micromeritics</a></li></ul></li> <li><a href="/wiki/Cryochemistry" title="Cryochemistry">Cryochemistry</a></li> <li><a href="/wiki/Sonochemistry" title="Sonochemistry">Sonochemistry</a></li> <li><a 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chemistry">Ceramic chemistry</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Stereochemistry" title="Stereochemistry">Stereochemistry</a> <ul><li><a href="/wiki/Alkane_stereochemistry" class="mw-redirect" title="Alkane stereochemistry">Alkane stereochemistry</a></li></ul></li> <li><a href="/wiki/Physical_organic_chemistry" title="Physical organic chemistry">Physical organic chemistry</a></li> <li><a href="/wiki/Organic_reactions" class="mw-redirect" title="Organic reactions">Organic reactions</a></li> <li><a href="/wiki/Organic_synthesis" title="Organic synthesis">Organic synthesis</a></li> <li><a href="/wiki/Retrosynthetic_analysis" title="Retrosynthetic analysis">Retrosynthetic analysis</a></li> <li><a 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title="Discovery of chemical elements">of element discoveries</a></li></ul></li> <li>"<a href="/wiki/The_central_science" title="The central science">The central science</a>"</li> <li><a href="/wiki/Chemical_reaction" title="Chemical reaction">Chemical reaction</a> <ul><li><a href="/wiki/Catalysis" title="Catalysis">Catalysis</a></li></ul></li> <li><a href="/wiki/Chemical_element" title="Chemical element">Chemical element</a></li> <li><a href="/wiki/Chemical_compound" title="Chemical compound">Chemical compound</a></li> <li><a href="/wiki/Atom" title="Atom">Atom</a></li> <li><a href="/wiki/Molecule" title="Molecule">Molecule</a></li> <li><a href="/wiki/Ion" title="Ion">Ion</a></li> <li><a href="/wiki/Chemical_substance" title="Chemical substance">Chemical substance</a></li> <li><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bond</a></li> <li><a href="/wiki/Alchemy" title="Alchemy">Alchemy</a></li> <li><a href="/wiki/Quantum_mechanics" title="Quantum mechanics">Quantum 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