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  • Biological Products/chemical synthesis/chemistry  (2)
  • *Synthetic Biology/economics/methods  (1)
  • Alkylation  (1)
  • 1
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    Total synthesis of eudesmane terpenes by site-selective C-H oxidations (2009)
    Nature Publishing Group (NPG)
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    Publication Date: 2009-05-15
    Description: From menthol to cholesterol to Taxol, terpenes are a ubiquitous group of molecules (over 55,000 members isolated so far) that have long provided humans with flavours, fragrances, hormones, medicines and even commercial products such as rubber. Although they possess a seemingly endless variety of architectural complexities, the biosynthesis of terpenes often occurs in a unified fashion as a 'two-phase' process. In the first phase (the cyclase phase), simple linear hydrocarbon phosphate building blocks are stitched together by means of 'prenyl coupling', followed by enzymatically controlled molecular cyclizations and rearrangements. In the second phase (the oxidase phase), oxidation of alkenes and carbon-hydrogen bonds results in a large array of structural diversity. Although organic chemists have made great progress in developing the logic needed for the cyclase phase of terpene synthesis, particularly in the area of polyene cyclizations, much remains to be learned if the oxidase phase is to be mimicked in the laboratory. Here we show how the logic of terpene biosynthesis has inspired the highly efficient and stereocontrolled syntheses of five oxidized members of the eudesmane family of terpenes in a modicum of steps by a series of simple carbocycle-forming reactions followed by multiple site-selective inter- and intramolecular carbon-hydrogen oxidations. This work establishes an intellectual framework in which to conceive the laboratory synthesis of other complex terpenes using a 'two-phase' approach.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Chen, Ke -- Baran, Phil S -- England -- Nature. 2009 Jun 11;459(7248):824-8. doi: 10.1038/nature08043. Epub 2009 May 13.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/19440196" target="_blank"〉PubMed〈/a〉
    Keywords: Biological Products/chemical synthesis/chemistry ; Biomimetics ; Carbon/*chemistry ; Hydrogen/*chemistry ; Molecular Structure ; Oxidation-Reduction ; Sesquiterpenes/chemical synthesis/chemistry ; Sesquiterpenes, Eudesmane/*chemical synthesis/*chemistry
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Published by Nature Publishing Group (NPG)
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  • 2
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    Synthesis: A constructive debate (2012)
    Nature Publishing Group (NPG)
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    Publication Date: 2012-12-14
    Description: 〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Keasling, Jay D -- Mendoza, Abraham -- Baran, Phil S -- England -- Nature. 2012 Dec 13;492(7428):188-9. doi: 10.1038/492188a.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/23235869" target="_blank"〉PubMed〈/a〉
    Keywords: Biotechnology/economics/*trends ; Chemistry Techniques, Synthetic/economics/*methods/trends ; *Synthetic Biology/economics/methods
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Published by Nature Publishing Group (NPG)
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  • 3
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    Practical and innate carbon-hydrogen functionalization of heterocycles (2012)
    Nature Publishing Group (NPG)
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    Publication Date: 2012-12-04
    Description: Nitrogen-rich heterocyclic compounds have had a profound effect on human health because these chemical motifs are found in a large number of drugs used to combat a broad range of diseases and pathophysiological conditions. Advances in transition-metal-mediated cross-coupling have simplified the synthesis of such molecules; however, C-H functionalization of medicinally important heterocycles that does not rely on pre-functionalized starting materials is an underdeveloped area. Unfortunately, the innate properties of heterocycles that make them so desirable for biological applications--such as aqueous solubility and their ability to act as ligands--render them challenging substrates for direct chemical functionalization. Here we report that zinc sulphinate salts can be used to transfer alkyl radicals to heterocycles, allowing for the mild (moderate temperature, 50 degrees C or less), direct and operationally simple formation of medicinally relevant C-C bonds while reacting in a complementary fashion to other innate C-H functionalization methods (Minisci, borono-Minisci, electrophilic aromatic substitution, transition-metal-mediated C-H insertion and C-H deprotonation). We prepared a toolkit of these reagents and studied their reactivity across a wide range of heterocycles (natural products, drugs and building blocks) without recourse to protecting-group chemistry. The reagents can even be used in tandem fashion in a single pot in the presence of water and air.〈br /〉〈br /〉〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3518649/" target="_blank"〉〈img src="https://static.pubmed.gov/portal/portal3rc.fcgi/4089621/img/3977009" border="0"〉〈/a〉   〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3518649/" target="_blank"〉This paper as free author manuscript - peer-reviewed and accepted for publication〈/a〉〈br /〉〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Fujiwara, Yuta -- Dixon, Janice A -- O'Hara, Fionn -- Funder, Erik Daa -- Dixon, Darryl D -- Rodriguez, Rodrigo A -- Baxter, Ryan D -- Herle, Bart -- Sach, Neal -- Collins, Michael R -- Ishihara, Yoshihiro -- Baran, Phil S -- GM-073949/GM/NIGMS NIH HHS/ -- R01 GM073949/GM/NIGMS NIH HHS/ -- England -- Nature. 2012 Dec 6;492(7427):95-9. doi: 10.1038/nature11680. Epub 2012 Nov 28.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/23201691" target="_blank"〉PubMed〈/a〉
    Keywords: Air ; Alkylation ; Biological Products/chemistry ; Carbon/*chemistry ; Drug Design ; Hydrogen/*chemistry ; Hydrogen Bonding ; Indicators and Reagents/chemistry ; Methylation ; Nitrogen/chemistry ; Pharmaceutical Preparations/chemistry ; Sulfinic Acids/chemistry ; Water ; Zinc/chemistry
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Published by Nature Publishing Group (NPG)
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  • 4
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    Scalable and sustainable electrochemical allylic C-H oxidation (2016)
    Nature Publishing Group (NPG)
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    Publication Date: 2016-04-21
    Description: New methods and strategies for the direct functionalization of C-H bonds are beginning to reshape the field of retrosynthetic analysis, affecting the synthesis of natural products, medicines and materials. The oxidation of allylic systems has played a prominent role in this context as possibly the most widely applied C-H functionalization, owing to the utility of enones and allylic alcohols as versatile intermediates, and their prevalence in natural and unnatural materials. Allylic oxidations have featured in hundreds of syntheses, including some natural product syntheses regarded as "classics". Despite many attempts to improve the efficiency and practicality of this transformation, the majority of conditions still use highly toxic reagents (based around toxic elements such as chromium or selenium) or expensive catalysts (such as palladium or rhodium). These requirements are problematic in industrial settings; currently, no scalable and sustainable solution to allylic oxidation exists. This oxidation strategy is therefore rarely used for large-scale synthetic applications, limiting the adoption of this retrosynthetic strategy by industrial scientists. Here we describe an electrochemical C-H oxidation strategy that exhibits broad substrate scope, operational simplicity and high chemoselectivity. It uses inexpensive and readily available materials, and represents a scalable allylic C-H oxidation (demonstrated on 100 grams), enabling the adoption of this C-H oxidation strategy in large-scale industrial settings without substantial environmental impact.〈br /〉〈br /〉〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4860034/" target="_blank"〉〈img src="https://static.pubmed.gov/portal/portal3rc.fcgi/4089621/img/3977009" border="0"〉〈/a〉   〈a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4860034/" target="_blank"〉This paper as free author manuscript - peer-reviewed and accepted for publication〈/a〉〈br /〉〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Horn, Evan J -- Rosen, Brandon R -- Chen, Yong -- Tang, Jiaze -- Chen, Ke -- Eastgate, Martin D -- Baran, Phil S -- GM-097444/GM/NIGMS NIH HHS/ -- R01 GM073949/GM/NIGMS NIH HHS/ -- R01 GM097444/GM/NIGMS NIH HHS/ -- England -- Nature. 2016 May 5;533(7601):77-81. doi: 10.1038/nature17431. Epub 2016 Apr 20.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA. ; Asymchem Life Science (Tianjin), Tianjin Economic-Technological Development Zone, Tianjin 300457, China. ; Chemical Development, Bristol-Myers Squibb, New Brunswick, New Jersey 08903, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/27096371" target="_blank"〉PubMed〈/a〉
    Keywords: Allyl Compounds/chemistry ; Biological Products/chemical synthesis/chemistry ; Carbon/*chemistry ; *Chemistry Techniques, Synthetic ; Electrochemistry ; Green Chemistry Technology ; Hydrogen/*chemistry ; Oxidants/*chemistry ; Oxidation-Reduction ; Substrate Specificity
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Published by Nature Publishing Group (NPG)
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