Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A
An effective total synthesis of (−)-9-deoxy-englerin (4), an analogue of the natural guaiane sesquiterpene englerin A (1), has been achieved. The synthesis features a transannular epoxide opening to construct the 5,7-fused ring system followed by transannular ether formation with mercury(II) trifluo...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2011-04, Vol.13 (8), p.2090-2093 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2093 |
|---|---|
| container_issue | 8 |
| container_start_page | 2090 |
| container_title | Organic letters |
| container_volume | 13 |
| creator | Ushakov, Dmitry B Navickas, Vaidotas Ströbele, Markus Maichle-Mössmer, Cäcilia Sasse, Florenz Maier, Martin E |
| description | An effective total synthesis of (−)-9-deoxy-englerin (4), an analogue of the natural guaiane sesquiterpene englerin A (1), has been achieved. The synthesis features a transannular epoxide opening to construct the 5,7-fused ring system followed by transannular ether formation with mercury(II) trifluoroacetate. |
| doi_str_mv | 10.1021/ol200499t |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_868768664</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>868768664</sourcerecordid><originalsourceid>FETCH-LOGICAL-a380t-77dbabecaaff961b7afc5fa121e3994ad21ad35a6deb5db9e3d5583f7a8ee8093</originalsourceid><addsrcrecordid>eNptkE1OwzAQRi0EoqWw4AIoGwRdBOw4ceJlKeVHqsSCso4m8bikcu0SJ4jegDVH5CQEtXTFakbzPX3SPEJOGb1iNGLXzkSUxlI2e6TPkoiHKU2i_d0uaI8ceb-glHUXeUh6EYsZFzLuk8nMNWCC57VtXtFXPgCrgpvKGTevyi6YvINpoamcDZwOLr8_v4ahDG_RfaxDtHODdWWD0TE50GA8nmzngLzcTWbjh3D6dP84Hk1D4BltwjRVBRRYAmgtBStS0GWigUUMuZQxqIiB4gkIhUWiColcJUnGdQoZYkYlH5CLTe-qdm8t-iZfVr5EY8Cia32eiSwVmRBxRw43ZFk772vU-aqullCvc0bzX2n5TlrHnm1b22KJakf-WeqA8w0Apc8Xrq1t9-Q_RT9KqnQS</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>868768664</pqid></control><display><type>article</type><title>Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A</title><source>ACS Publications</source><source>MEDLINE</source><creator>Ushakov, Dmitry B ; Navickas, Vaidotas ; Ströbele, Markus ; Maichle-Mössmer, Cäcilia ; Sasse, Florenz ; Maier, Martin E</creator><creatorcontrib>Ushakov, Dmitry B ; Navickas, Vaidotas ; Ströbele, Markus ; Maichle-Mössmer, Cäcilia ; Sasse, Florenz ; Maier, Martin E</creatorcontrib><description>An effective total synthesis of (−)-9-deoxy-englerin (4), an analogue of the natural guaiane sesquiterpene englerin A (1), has been achieved. The synthesis features a transannular epoxide opening to construct the 5,7-fused ring system followed by transannular ether formation with mercury(II) trifluoroacetate.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol200499t</identifier><identifier>PMID: 21413694</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkylation ; Cell Line ; Cell Proliferation - drug effects ; Cyclization ; Humans ; Models, Molecular ; Molecular Structure ; Sesquiterpenes, Guaiane - chemical synthesis ; Sesquiterpenes, Guaiane - pharmacology</subject><ispartof>Organic letters, 2011-04, Vol.13 (8), p.2090-2093</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2011 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a380t-77dbabecaaff961b7afc5fa121e3994ad21ad35a6deb5db9e3d5583f7a8ee8093</citedby><cites>FETCH-LOGICAL-a380t-77dbabecaaff961b7afc5fa121e3994ad21ad35a6deb5db9e3d5583f7a8ee8093</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/ol200499t$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol200499t$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21413694$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ushakov, Dmitry B</creatorcontrib><creatorcontrib>Navickas, Vaidotas</creatorcontrib><creatorcontrib>Ströbele, Markus</creatorcontrib><creatorcontrib>Maichle-Mössmer, Cäcilia</creatorcontrib><creatorcontrib>Sasse, Florenz</creatorcontrib><creatorcontrib>Maier, Martin E</creatorcontrib><title>Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>An effective total synthesis of (−)-9-deoxy-englerin (4), an analogue of the natural guaiane sesquiterpene englerin A (1), has been achieved. The synthesis features a transannular epoxide opening to construct the 5,7-fused ring system followed by transannular ether formation with mercury(II) trifluoroacetate.</description><subject>Alkylation</subject><subject>Cell Line</subject><subject>Cell Proliferation - drug effects</subject><subject>Cyclization</subject><subject>Humans</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Sesquiterpenes, Guaiane - chemical synthesis</subject><subject>Sesquiterpenes, Guaiane - pharmacology</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1OwzAQRi0EoqWw4AIoGwRdBOw4ceJlKeVHqsSCso4m8bikcu0SJ4jegDVH5CQEtXTFakbzPX3SPEJOGb1iNGLXzkSUxlI2e6TPkoiHKU2i_d0uaI8ceb-glHUXeUh6EYsZFzLuk8nMNWCC57VtXtFXPgCrgpvKGTevyi6YvINpoamcDZwOLr8_v4ahDG_RfaxDtHODdWWD0TE50GA8nmzngLzcTWbjh3D6dP84Hk1D4BltwjRVBRRYAmgtBStS0GWigUUMuZQxqIiB4gkIhUWiColcJUnGdQoZYkYlH5CLTe-qdm8t-iZfVr5EY8Cia32eiSwVmRBxRw43ZFk772vU-aqullCvc0bzX2n5TlrHnm1b22KJakf-WeqA8w0Apc8Xrq1t9-Q_RT9KqnQS</recordid><startdate>20110415</startdate><enddate>20110415</enddate><creator>Ushakov, Dmitry B</creator><creator>Navickas, Vaidotas</creator><creator>Ströbele, Markus</creator><creator>Maichle-Mössmer, Cäcilia</creator><creator>Sasse, Florenz</creator><creator>Maier, Martin E</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>20110415</creationdate><title>Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A</title><author>Ushakov, Dmitry B ; Navickas, Vaidotas ; Ströbele, Markus ; Maichle-Mössmer, Cäcilia ; Sasse, Florenz ; Maier, Martin E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-77dbabecaaff961b7afc5fa121e3994ad21ad35a6deb5db9e3d5583f7a8ee8093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alkylation</topic><topic>Cell Line</topic><topic>Cell Proliferation - drug effects</topic><topic>Cyclization</topic><topic>Humans</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Sesquiterpenes, Guaiane - chemical synthesis</topic><topic>Sesquiterpenes, Guaiane - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ushakov, Dmitry B</creatorcontrib><creatorcontrib>Navickas, Vaidotas</creatorcontrib><creatorcontrib>Ströbele, Markus</creatorcontrib><creatorcontrib>Maichle-Mössmer, Cäcilia</creatorcontrib><creatorcontrib>Sasse, Florenz</creatorcontrib><creatorcontrib>Maier, Martin E</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>Ushakov, Dmitry B</au><au>Navickas, Vaidotas</au><au>Ströbele, Markus</au><au>Maichle-Mössmer, Cäcilia</au><au>Sasse, Florenz</au><au>Maier, Martin E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2011-04-15</date><risdate>2011</risdate><volume>13</volume><issue>8</issue><spage>2090</spage><epage>2093</epage><pages>2090-2093</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An effective total synthesis of (−)-9-deoxy-englerin (4), an analogue of the natural guaiane sesquiterpene englerin A (1), has been achieved. The synthesis features a transannular epoxide opening to construct the 5,7-fused ring system followed by transannular ether formation with mercury(II) trifluoroacetate.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>21413694</pmid><doi>10.1021/ol200499t</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2011-04, Vol.13 (8), p.2090-2093 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_868768664 |
| source | ACS Publications; MEDLINE |
| subjects | Alkylation Cell Line Cell Proliferation - drug effects Cyclization Humans Models, Molecular Molecular Structure Sesquiterpenes, Guaiane - chemical synthesis Sesquiterpenes, Guaiane - pharmacology |
| title | Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T04%3A37%3A23IST&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=Total%20Synthesis%20and%20Biological%20Evaluation%20of%20(%E2%88%92)-9-Deoxy-englerin%20A&rft.jtitle=Organic%20letters&rft.au=Ushakov,%20Dmitry%20B&rft.date=2011-04-15&rft.volume=13&rft.issue=8&rft.spage=2090&rft.epage=2093&rft.pages=2090-2093&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol200499t&rft_dat=%3Cproquest_cross%3E868768664%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=868768664&rft_id=info:pmid/21413694&rfr_iscdi=true |