Loading…
Total synthesis of eudesmane terpenes by site-selective C-H oxidations
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 arc...
Saved in:
Published in: | Nature (London) 2009-06, Vol.459 (7248), p.824-828 |
---|---|
Main Authors: | , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-c647t-f7a519d5da5d77b594d7872c94a70c99771d64748dafa828cc1bb8d4f568f6e3 |
---|---|
cites | cdi_FETCH-LOGICAL-c647t-f7a519d5da5d77b594d7872c94a70c99771d64748dafa828cc1bb8d4f568f6e3 |
container_end_page | 828 |
container_issue | 7248 |
container_start_page | 824 |
container_title | Nature (London) |
container_volume | 459 |
creator | Chen, Ke Baran, Phil S |
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. |
doi_str_mv | 10.1038/nature08043 |
format | article |
fullrecord | <record><control><sourceid>gale_proqu</sourceid><recordid>TN_cdi_proquest_miscellaneous_67364004</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><galeid>A202125815</galeid><sourcerecordid>A202125815</sourcerecordid><originalsourceid>FETCH-LOGICAL-c647t-f7a519d5da5d77b594d7872c94a70c99771d64748dafa828cc1bb8d4f568f6e3</originalsourceid><addsrcrecordid>eNp10t2LEzEQAPAgilerT77LeqAgumeym02yj6V43sGhoAUfl2wyW3PsRy-Tlet_b44t11YqeQgkv8xMhiHkNaMXjObqc6_D6IEqyvMnZMa4FCkXSj4lM0ozlVKVizPyAvGWUlowyZ-TM1ZyTlkpZuRyNQTdJrjtw29Ah8nQJDBawE73kATwG-gBk3qboAuQIrRggvsDyTK9SoZ7Z3VwQ48vybNGtwivdvucrC6_rJZX6c33r9fLxU1qBJchbaQuWGkLqwsrZV2U3EolM1NyLakpSymZjZArqxutMmUMq2tleVMI1QjI5-T9FHbjh7sRMFSdQwNtG4sdRqyEzAWnsRFzcv4PvB1G38fSqoxyLnKRq4jSCa11C5XrmyF4bdbxw163Qw-Ni8eLjGYsKxQr9kGPvNm4u-oQXZxAcVnonDkZ9cPRg2gC3Ie1HhGr658_ju3H_9vF6tfy20lt_IDooak23nXabytGq4fRqQ5GJ-o3u5aNdQd2b3ezEsG7HdBodNt43RuHjy6LGbMsf-j9p8lhvOrX4Pe9P5337cSnw8d4h-YvHK3ixA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>204463638</pqid></control><display><type>article</type><title>Total synthesis of eudesmane terpenes by site-selective C-H oxidations</title><source>Nature Journals</source><creator>Chen, Ke ; Baran, Phil S</creator><creatorcontrib>Chen, Ke ; Baran, Phil S</creatorcontrib><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.</description><identifier>ISSN: 0028-0836</identifier><identifier>EISSN: 1476-4687</identifier><identifier>DOI: 10.1038/nature08043</identifier><identifier>PMID: 19440196</identifier><identifier>CODEN: NATUAS</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids ; Alkenes ; Biological Products - chemical synthesis ; Biological Products - chemistry ; Biomimetics ; Biosynthesis ; Carbon - chemistry ; Chemical synthesis ; Chemistry ; Exact sciences and technology ; Hormones ; Humanities and Social Sciences ; Hydrogen - chemistry ; letter ; Mass spectrometry ; Molecular Structure ; Molecular weight ; multidisciplinary ; Natural products ; Organic chemistry ; Organic compounds ; Oxidation ; Oxidation-Reduction ; Oxidation-reduction reaction ; Physiological aspects ; Preparations and properties ; Science ; Science (multidisciplinary) ; Sesquiterpenes - chemical synthesis ; Sesquiterpenes - chemistry ; Sesquiterpenes, Eudesmane - chemical synthesis ; Sesquiterpenes, Eudesmane - chemistry ; Steroids ; Synthesis ; Terpenes</subject><ispartof>Nature (London), 2009-06, Vol.459 (7248), p.824-828</ispartof><rights>Macmillan Publishers Limited. All rights reserved 2009</rights><rights>2009 INIST-CNRS</rights><rights>COPYRIGHT 2009 Nature Publishing Group</rights><rights>Copyright Nature Publishing Group Jun 11, 2009</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c647t-f7a519d5da5d77b594d7872c94a70c99771d64748dafa828cc1bb8d4f568f6e3</citedby><cites>FETCH-LOGICAL-c647t-f7a519d5da5d77b594d7872c94a70c99771d64748dafa828cc1bb8d4f568f6e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,2725,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21532234$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19440196$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Ke</creatorcontrib><creatorcontrib>Baran, Phil S</creatorcontrib><title>Total synthesis of eudesmane terpenes by site-selective C-H oxidations</title><title>Nature (London)</title><addtitle>Nature</addtitle><addtitle>Nature</addtitle><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.</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Alkenes</subject><subject>Biological Products - chemical synthesis</subject><subject>Biological Products - chemistry</subject><subject>Biomimetics</subject><subject>Biosynthesis</subject><subject>Carbon - chemistry</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Hormones</subject><subject>Humanities and Social Sciences</subject><subject>Hydrogen - chemistry</subject><subject>letter</subject><subject>Mass spectrometry</subject><subject>Molecular Structure</subject><subject>Molecular weight</subject><subject>multidisciplinary</subject><subject>Natural products</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Oxidation</subject><subject>Oxidation-Reduction</subject><subject>Oxidation-reduction reaction</subject><subject>Physiological aspects</subject><subject>Preparations and properties</subject><subject>Science</subject><subject>Science (multidisciplinary)</subject><subject>Sesquiterpenes - chemical synthesis</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes, Eudesmane - chemical synthesis</subject><subject>Sesquiterpenes, Eudesmane - chemistry</subject><subject>Steroids</subject><subject>Synthesis</subject><subject>Terpenes</subject><issn>0028-0836</issn><issn>1476-4687</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNp10t2LEzEQAPAgilerT77LeqAgumeym02yj6V43sGhoAUfl2wyW3PsRy-Tlet_b44t11YqeQgkv8xMhiHkNaMXjObqc6_D6IEqyvMnZMa4FCkXSj4lM0ozlVKVizPyAvGWUlowyZ-TM1ZyTlkpZuRyNQTdJrjtw29Ah8nQJDBawE73kATwG-gBk3qboAuQIrRggvsDyTK9SoZ7Z3VwQ48vybNGtwivdvucrC6_rJZX6c33r9fLxU1qBJchbaQuWGkLqwsrZV2U3EolM1NyLakpSymZjZArqxutMmUMq2tleVMI1QjI5-T9FHbjh7sRMFSdQwNtG4sdRqyEzAWnsRFzcv4PvB1G38fSqoxyLnKRq4jSCa11C5XrmyF4bdbxw163Qw-Ni8eLjGYsKxQr9kGPvNm4u-oQXZxAcVnonDkZ9cPRg2gC3Ie1HhGr658_ju3H_9vF6tfy20lt_IDooak23nXabytGq4fRqQ5GJ-o3u5aNdQd2b3ezEsG7HdBodNt43RuHjy6LGbMsf-j9p8lhvOrX4Pe9P5337cSnw8d4h-YvHK3ixA</recordid><startdate>20090611</startdate><enddate>20090611</enddate><creator>Chen, Ke</creator><creator>Baran, Phil S</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>ATWCN</scope><scope>3V.</scope><scope>7QG</scope><scope>7QL</scope><scope>7QP</scope><scope>7QR</scope><scope>7RV</scope><scope>7SN</scope><scope>7SS</scope><scope>7ST</scope><scope>7T5</scope><scope>7TG</scope><scope>7TK</scope><scope>7TM</scope><scope>7TO</scope><scope>7U9</scope><scope>7X2</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>88G</scope><scope>88I</scope><scope>8AF</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>ATCPS</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>KB.</scope><scope>KB0</scope><scope>KL.</scope><scope>L6V</scope><scope>LK8</scope><scope>M0K</scope><scope>M0S</scope><scope>M1P</scope><scope>M2M</scope><scope>M2O</scope><scope>M2P</scope><scope>M7N</scope><scope>M7P</scope><scope>M7S</scope><scope>MBDVC</scope><scope>NAPCQ</scope><scope>P5Z</scope><scope>P62</scope><scope>P64</scope><scope>PATMY</scope><scope>PCBAR</scope><scope>PDBOC</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PSYQQ</scope><scope>PTHSS</scope><scope>PYCSY</scope><scope>Q9U</scope><scope>R05</scope><scope>RC3</scope><scope>S0X</scope><scope>SOI</scope><scope>7X8</scope></search><sort><creationdate>20090611</creationdate><title>Total synthesis of eudesmane terpenes by site-selective C-H oxidations</title><author>Chen, Ke ; Baran, Phil S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c647t-f7a519d5da5d77b594d7872c94a70c99771d64748dafa828cc1bb8d4f568f6e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Alkenes</topic><topic>Biological Products - chemical synthesis</topic><topic>Biological Products - chemistry</topic><topic>Biomimetics</topic><topic>Biosynthesis</topic><topic>Carbon - chemistry</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Hormones</topic><topic>Humanities and Social Sciences</topic><topic>Hydrogen - chemistry</topic><topic>letter</topic><topic>Mass spectrometry</topic><topic>Molecular Structure</topic><topic>Molecular weight</topic><topic>multidisciplinary</topic><topic>Natural products</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Oxidation</topic><topic>Oxidation-Reduction</topic><topic>Oxidation-reduction reaction</topic><topic>Physiological aspects</topic><topic>Preparations and properties</topic><topic>Science</topic><topic>Science (multidisciplinary)</topic><topic>Sesquiterpenes - chemical synthesis</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes, Eudesmane - chemical synthesis</topic><topic>Sesquiterpenes, Eudesmane - chemistry</topic><topic>Steroids</topic><topic>Synthesis</topic><topic>Terpenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Ke</creatorcontrib><creatorcontrib>Baran, Phil S</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Gale In Context: Middle School</collection><collection>ProQuest Central (Corporate)</collection><collection>Animal Behavior Abstracts</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Proquest Nursing & Allied Health Source</collection><collection>Ecology Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Environment Abstracts</collection><collection>Immunology Abstracts</collection><collection>Meteorological & Geoastrophysical Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Oncogenes and Growth Factors Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Agricultural Science Collection</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Psychology Database (Alumni)</collection><collection>Science Database (Alumni Edition)</collection><collection>STEM Database</collection><collection>ProQuest Pharma Collection</collection><collection>Public Health Database</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central</collection><collection>Advanced Technologies & Aerospace Collection</collection><collection>Agricultural & Environmental Science Collection</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>eLibrary</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Materials Science Database</collection><collection>Nursing & Allied Health Database (Alumni Edition)</collection><collection>Meteorological & Geoastrophysical Abstracts - Academic</collection><collection>ProQuest Engineering Collection</collection><collection>Biological Sciences</collection><collection>Agriculture Science Database</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Psychology Database (ProQuest)</collection><collection>Research Library</collection><collection>Science Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</collection><collection>Engineering Database</collection><collection>Research Library (Corporate)</collection><collection>Nursing & Allied Health Premium</collection><collection>Advanced Technologies & Aerospace Database</collection><collection>ProQuest Advanced Technologies & Aerospace Collection</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environmental Science Database</collection><collection>Earth, Atmospheric & Aquatic Science Database</collection><collection>Materials Science Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest One Psychology</collection><collection>Engineering Collection</collection><collection>Environmental Science Collection</collection><collection>ProQuest Central Basic</collection><collection>University of Michigan</collection><collection>Genetics Abstracts</collection><collection>SIRS Editorial</collection><collection>Environment Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Nature (London)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Ke</au><au>Baran, Phil S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total synthesis of eudesmane terpenes by site-selective C-H oxidations</atitle><jtitle>Nature (London)</jtitle><stitle>Nature</stitle><addtitle>Nature</addtitle><date>2009-06-11</date><risdate>2009</risdate><volume>459</volume><issue>7248</issue><spage>824</spage><epage>828</epage><pages>824-828</pages><issn>0028-0836</issn><eissn>1476-4687</eissn><coden>NATUAS</coden><abstract>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.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>19440196</pmid><doi>10.1038/nature08043</doi><tpages>5</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0028-0836 |
ispartof | Nature (London), 2009-06, Vol.459 (7248), p.824-828 |
issn | 0028-0836 1476-4687 |
language | eng |
recordid | cdi_proquest_miscellaneous_67364004 |
source | Nature Journals |
subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Alkenes Biological Products - chemical synthesis Biological Products - chemistry Biomimetics Biosynthesis Carbon - chemistry Chemical synthesis Chemistry Exact sciences and technology Hormones Humanities and Social Sciences Hydrogen - chemistry letter Mass spectrometry Molecular Structure Molecular weight multidisciplinary Natural products Organic chemistry Organic compounds Oxidation Oxidation-Reduction Oxidation-reduction reaction Physiological aspects Preparations and properties Science Science (multidisciplinary) Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Sesquiterpenes, Eudesmane - chemical synthesis Sesquiterpenes, Eudesmane - chemistry Steroids Synthesis Terpenes |
title | Total synthesis of eudesmane terpenes by site-selective C-H oxidations |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-11T19%3A00%3A24IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-gale_proqu&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Total%20synthesis%20of%20eudesmane%20terpenes%20by%20site-selective%20C-H%20oxidations&rft.jtitle=Nature%20(London)&rft.au=Chen,%20Ke&rft.date=2009-06-11&rft.volume=459&rft.issue=7248&rft.spage=824&rft.epage=828&rft.pages=824-828&rft.issn=0028-0836&rft.eissn=1476-4687&rft.coden=NATUAS&rft_id=info:doi/10.1038/nature08043&rft_dat=%3Cgale_proqu%3EA202125815%3C/gale_proqu%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c647t-f7a519d5da5d77b594d7872c94a70c99771d64748dafa828cc1bb8d4f568f6e3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=204463638&rft_id=info:pmid/19440196&rft_galeid=A202125815&rfr_iscdi=true |