Conjugate Addition of 2- and 4-Pyridylcuprates: An Expeditious Asymmetric Synthesis of Natural (−)-Evoninic Acid
The scope and limitations of the conjugate addition of 2- and the first 4-pyridyl Gilman homocuprates to various α,β-unsaturated Michael acceptors are delineated. The conjugate addition of the cuprate of 2-bromo-3-methylpyridine to (E)-methyl crotonate then diastereoselective enolate alkylation and...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2007-03, Vol.9 (5), p.891-894 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 894 |
|---|---|
| container_issue | 5 |
| container_start_page | 891 |
| container_title | Organic letters |
| container_volume | 9 |
| creator | Spivey, Alan C Shukla, Lena Hayler, Judy F |
| description | The scope and limitations of the conjugate addition of 2- and the first 4-pyridyl Gilman homocuprates to various α,β-unsaturated Michael acceptors are delineated. The conjugate addition of the cuprate of 2-bromo-3-methylpyridine to (E)-methyl crotonate then diastereoselective enolate alkylation and lipase-mediated enantioselective ester hydrolysis have enabled an efficient four-step first asymmetric synthesis of the Celastraceae sesquiterpenoid esterifying ligand (−)-(1‘S,2‘S)-evoninic acid. |
| doi_str_mv | 10.1021/ol070011y |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_69037798</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>69037798</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-154ed30643251625d6ce97789352352386769bb8aacb39445e2b7501eb204c013</originalsourceid><addsrcrecordid>eNpt0E1LwzAYB_AgipvTg19AclHcoZqXtmm9lTFfYKignkuaZprRpjNpxN486tWPuE9i5sa8CA_kOfz4k-cPwCFGZxgRfN5UiCGEcbcF-jgiNGAoItubPUY9sGftbEkiku6CHmYkSUKK-sCNGj1zz7yVMCtL1apGw2YKSQC5LmEY3HdGlV0l3Nx4Yy8WH18w03D8Ppe_2lmY2a6uZWuUgA-dbl-kVXaZcctbZ3gFTxef38Ng_NZopb3JhCr3wc6UV1YerN8BeLocP46ug8nd1c0omwScsrQNcBTKkqI4pCTCMYnKWMiUsSSl_jA_SczitCgSzkVB0zCMJClYhLAsCAoFwnQATla5c9O8OmnbvFZWyKriWvqv53GKKGNp4uFwBYVprDVyms-NqrnpcozyZcf5pmNvj9ahrqhl-SfXpXpwvAJc2HzWOKP9jf8E_QAD4IL3</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>69037798</pqid></control><display><type>article</type><title>Conjugate Addition of 2- and 4-Pyridylcuprates: An Expeditious Asymmetric Synthesis of Natural (−)-Evoninic Acid</title><source>MEDLINE</source><source>American Chemical Society Publications</source><creator>Spivey, Alan C ; Shukla, Lena ; Hayler, Judy F</creator><creatorcontrib>Spivey, Alan C ; Shukla, Lena ; Hayler, Judy F</creatorcontrib><description>The scope and limitations of the conjugate addition of 2- and the first 4-pyridyl Gilman homocuprates to various α,β-unsaturated Michael acceptors are delineated. The conjugate addition of the cuprate of 2-bromo-3-methylpyridine to (E)-methyl crotonate then diastereoselective enolate alkylation and lipase-mediated enantioselective ester hydrolysis have enabled an efficient four-step first asymmetric synthesis of the Celastraceae sesquiterpenoid esterifying ligand (−)-(1‘S,2‘S)-evoninic acid.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol070011y</identifier><identifier>PMID: 17288430</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Biological Products - chemical synthesis ; Biological Products - chemistry ; Celastraceae - chemistry ; Celastraceae - metabolism ; Ether - chemistry ; Methylation ; Molecular Structure ; Propionates - chemical synthesis ; Propionates - chemistry ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2007-03, Vol.9 (5), p.891-894</ispartof><rights>Copyright © 2007 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-154ed30643251625d6ce97789352352386769bb8aacb39445e2b7501eb204c013</citedby><cites>FETCH-LOGICAL-a379t-154ed30643251625d6ce97789352352386769bb8aacb39445e2b7501eb204c013</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol070011y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol070011y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17288430$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Spivey, Alan C</creatorcontrib><creatorcontrib>Shukla, Lena</creatorcontrib><creatorcontrib>Hayler, Judy F</creatorcontrib><title>Conjugate Addition of 2- and 4-Pyridylcuprates: An Expeditious Asymmetric Synthesis of Natural (−)-Evoninic Acid</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The scope and limitations of the conjugate addition of 2- and the first 4-pyridyl Gilman homocuprates to various α,β-unsaturated Michael acceptors are delineated. The conjugate addition of the cuprate of 2-bromo-3-methylpyridine to (E)-methyl crotonate then diastereoselective enolate alkylation and lipase-mediated enantioselective ester hydrolysis have enabled an efficient four-step first asymmetric synthesis of the Celastraceae sesquiterpenoid esterifying ligand (−)-(1‘S,2‘S)-evoninic acid.</description><subject>Biological Products - chemical synthesis</subject><subject>Biological Products - chemistry</subject><subject>Celastraceae - chemistry</subject><subject>Celastraceae - metabolism</subject><subject>Ether - chemistry</subject><subject>Methylation</subject><subject>Molecular Structure</subject><subject>Propionates - chemical synthesis</subject><subject>Propionates - chemistry</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1LwzAYB_AgipvTg19AclHcoZqXtmm9lTFfYKignkuaZprRpjNpxN486tWPuE9i5sa8CA_kOfz4k-cPwCFGZxgRfN5UiCGEcbcF-jgiNGAoItubPUY9sGftbEkiku6CHmYkSUKK-sCNGj1zz7yVMCtL1apGw2YKSQC5LmEY3HdGlV0l3Nx4Yy8WH18w03D8Ppe_2lmY2a6uZWuUgA-dbl-kVXaZcctbZ3gFTxef38Ng_NZopb3JhCr3wc6UV1YerN8BeLocP46ug8nd1c0omwScsrQNcBTKkqI4pCTCMYnKWMiUsSSl_jA_SczitCgSzkVB0zCMJClYhLAsCAoFwnQATla5c9O8OmnbvFZWyKriWvqv53GKKGNp4uFwBYVprDVyms-NqrnpcozyZcf5pmNvj9ahrqhl-SfXpXpwvAJc2HzWOKP9jf8E_QAD4IL3</recordid><startdate>20070301</startdate><enddate>20070301</enddate><creator>Spivey, Alan C</creator><creator>Shukla, Lena</creator><creator>Hayler, Judy F</creator><general>American Chemical Society</general><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>7X8</scope></search><sort><creationdate>20070301</creationdate><title>Conjugate Addition of 2- and 4-Pyridylcuprates: An Expeditious Asymmetric Synthesis of Natural (−)-Evoninic Acid</title><author>Spivey, Alan C ; Shukla, Lena ; Hayler, Judy F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-154ed30643251625d6ce97789352352386769bb8aacb39445e2b7501eb204c013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Biological Products - chemical synthesis</topic><topic>Biological Products - chemistry</topic><topic>Celastraceae - chemistry</topic><topic>Celastraceae - metabolism</topic><topic>Ether - chemistry</topic><topic>Methylation</topic><topic>Molecular Structure</topic><topic>Propionates - chemical synthesis</topic><topic>Propionates - chemistry</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Spivey, Alan C</creatorcontrib><creatorcontrib>Shukla, Lena</creatorcontrib><creatorcontrib>Hayler, Judy F</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Spivey, Alan C</au><au>Shukla, Lena</au><au>Hayler, Judy F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Conjugate Addition of 2- and 4-Pyridylcuprates: An Expeditious Asymmetric Synthesis of Natural (−)-Evoninic Acid</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2007-03-01</date><risdate>2007</risdate><volume>9</volume><issue>5</issue><spage>891</spage><epage>894</epage><pages>891-894</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The scope and limitations of the conjugate addition of 2- and the first 4-pyridyl Gilman homocuprates to various α,β-unsaturated Michael acceptors are delineated. The conjugate addition of the cuprate of 2-bromo-3-methylpyridine to (E)-methyl crotonate then diastereoselective enolate alkylation and lipase-mediated enantioselective ester hydrolysis have enabled an efficient four-step first asymmetric synthesis of the Celastraceae sesquiterpenoid esterifying ligand (−)-(1‘S,2‘S)-evoninic acid.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>17288430</pmid><doi>10.1021/ol070011y</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2007-03, Vol.9 (5), p.891-894 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69037798 |
| source | MEDLINE; American Chemical Society Publications |
| subjects | Biological Products - chemical synthesis Biological Products - chemistry Celastraceae - chemistry Celastraceae - metabolism Ether - chemistry Methylation Molecular Structure Propionates - chemical synthesis Propionates - chemistry Pyridines - chemical synthesis Pyridines - chemistry Stereoisomerism |
| title | Conjugate Addition of 2- and 4-Pyridylcuprates: An Expeditious Asymmetric Synthesis of Natural (−)-Evoninic Acid |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T07%3A04%3A31IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Conjugate%20Addition%20of%202-%20and%204-Pyridylcuprates:%E2%80%89%20An%20Expeditious%20Asymmetric%20Synthesis%20of%20Natural%20(%E2%88%92)-Evoninic%20Acid&rft.jtitle=Organic%20letters&rft.au=Spivey,%20Alan%20C&rft.date=2007-03-01&rft.volume=9&rft.issue=5&rft.spage=891&rft.epage=894&rft.pages=891-894&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol070011y&rft_dat=%3Cproquest_cross%3E69037798%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=69037798&rft_id=info:pmid/17288430&rfr_iscdi=true |