Total Synthesis of (±)-Clavubicyclone
The total synthesis of racemic clavubicyclone (1), which was isolated from Okinawan soft coral by our group, is described. The bicyclo[3.2.1]octane skeleton was prepared by Cope rearrangement of a divinylcyclopropane derivative. Three functional groups on the skeleton were constructed by Barton deca...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2006-10, Vol.8 (21), p.4883-4885 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4885 |
|---|---|
| container_issue | 21 |
| container_start_page | 4883 |
| container_title | Organic letters |
| container_volume | 8 |
| creator | Ito, Hisanaka Takeguchi, Shunta Kawagishi, Takahiro Iguchi, Kazuo |
| description | The total synthesis of racemic clavubicyclone (1), which was isolated from Okinawan soft coral by our group, is described. The bicyclo[3.2.1]octane skeleton was prepared by Cope rearrangement of a divinylcyclopropane derivative. Three functional groups on the skeleton were constructed by Barton decarboxylation, Wittig reaction, and alkylation. |
| doi_str_mv | 10.1021/ol061947u |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68933646</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68933646</sourcerecordid><originalsourceid>FETCH-LOGICAL-a313t-e9bdeaad8c0aa057118ad6eabc0ba94bdc3dc79ceb60c531534d2dfa47b787043</originalsourceid><addsrcrecordid>eNptkM1Kw0AQgBdRbK0efAHpxWIP0dlsspscS_EPCh6s52X2J5iyzdZsIvSxfAWfzEhCvXiaYfj4YD5CLincUojpnXfAaZ6I9oiMaRqzSEAaHx92DiNyFsIGgHaX_JSMqIAYWCzGZLb2Dbrp675q3m0ow9QX05vvr3m0dPjZqlLvtfOVPScnBbpgL4Y5IW8P9-vlU7R6eXxeLlYRMsqayObKWESTaUCEVFCaoeEWlQaFeaKMZkaLXFvFQaeMpiwxsSkwEUpkAhI2IbPeu6v9R2tDI7dl0NY5rKxvg-RZzhhPeAfOe1DXPoTaFnJXl1us95KC_I0iD1E69mqQtmprzR85VOiA6x5AHeTGt3XV_fiP6AeGR2iV</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68933646</pqid></control><display><type>article</type><title>Total Synthesis of (±)-Clavubicyclone</title><source>MEDLINE</source><source>ACS Publications</source><creator>Ito, Hisanaka ; Takeguchi, Shunta ; Kawagishi, Takahiro ; Iguchi, Kazuo</creator><creatorcontrib>Ito, Hisanaka ; Takeguchi, Shunta ; Kawagishi, Takahiro ; Iguchi, Kazuo</creatorcontrib><description>The total synthesis of racemic clavubicyclone (1), which was isolated from Okinawan soft coral by our group, is described. The bicyclo[3.2.1]octane skeleton was prepared by Cope rearrangement of a divinylcyclopropane derivative. Three functional groups on the skeleton were constructed by Barton decarboxylation, Wittig reaction, and alkylation.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol061947u</identifier><identifier>PMID: 17020327</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Anthozoa - chemistry ; Japan ; Molecular Structure ; Prostaglandins - chemical synthesis ; Prostaglandins - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2006-10, Vol.8 (21), p.4883-4885</ispartof><rights>Copyright © 2006 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a313t-e9bdeaad8c0aa057118ad6eabc0ba94bdc3dc79ceb60c531534d2dfa47b787043</citedby><cites>FETCH-LOGICAL-a313t-e9bdeaad8c0aa057118ad6eabc0ba94bdc3dc79ceb60c531534d2dfa47b787043</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/ol061947u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol061947u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17020327$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ito, Hisanaka</creatorcontrib><creatorcontrib>Takeguchi, Shunta</creatorcontrib><creatorcontrib>Kawagishi, Takahiro</creatorcontrib><creatorcontrib>Iguchi, Kazuo</creatorcontrib><title>Total Synthesis of (±)-Clavubicyclone</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The total synthesis of racemic clavubicyclone (1), which was isolated from Okinawan soft coral by our group, is described. The bicyclo[3.2.1]octane skeleton was prepared by Cope rearrangement of a divinylcyclopropane derivative. Three functional groups on the skeleton were constructed by Barton decarboxylation, Wittig reaction, and alkylation.</description><subject>Animals</subject><subject>Anthozoa - chemistry</subject><subject>Japan</subject><subject>Molecular Structure</subject><subject>Prostaglandins - chemical synthesis</subject><subject>Prostaglandins - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1Kw0AQgBdRbK0efAHpxWIP0dlsspscS_EPCh6s52X2J5iyzdZsIvSxfAWfzEhCvXiaYfj4YD5CLincUojpnXfAaZ6I9oiMaRqzSEAaHx92DiNyFsIGgHaX_JSMqIAYWCzGZLb2Dbrp675q3m0ow9QX05vvr3m0dPjZqlLvtfOVPScnBbpgL4Y5IW8P9-vlU7R6eXxeLlYRMsqayObKWESTaUCEVFCaoeEWlQaFeaKMZkaLXFvFQaeMpiwxsSkwEUpkAhI2IbPeu6v9R2tDI7dl0NY5rKxvg-RZzhhPeAfOe1DXPoTaFnJXl1us95KC_I0iD1E69mqQtmprzR85VOiA6x5AHeTGt3XV_fiP6AeGR2iV</recordid><startdate>20061012</startdate><enddate>20061012</enddate><creator>Ito, Hisanaka</creator><creator>Takeguchi, Shunta</creator><creator>Kawagishi, Takahiro</creator><creator>Iguchi, Kazuo</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>20061012</creationdate><title>Total Synthesis of (±)-Clavubicyclone</title><author>Ito, Hisanaka ; Takeguchi, Shunta ; Kawagishi, Takahiro ; Iguchi, Kazuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-e9bdeaad8c0aa057118ad6eabc0ba94bdc3dc79ceb60c531534d2dfa47b787043</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Anthozoa - chemistry</topic><topic>Japan</topic><topic>Molecular Structure</topic><topic>Prostaglandins - chemical synthesis</topic><topic>Prostaglandins - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ito, Hisanaka</creatorcontrib><creatorcontrib>Takeguchi, Shunta</creatorcontrib><creatorcontrib>Kawagishi, Takahiro</creatorcontrib><creatorcontrib>Iguchi, Kazuo</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>Ito, Hisanaka</au><au>Takeguchi, Shunta</au><au>Kawagishi, Takahiro</au><au>Iguchi, Kazuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of (±)-Clavubicyclone</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2006-10-12</date><risdate>2006</risdate><volume>8</volume><issue>21</issue><spage>4883</spage><epage>4885</epage><pages>4883-4885</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The total synthesis of racemic clavubicyclone (1), which was isolated from Okinawan soft coral by our group, is described. The bicyclo[3.2.1]octane skeleton was prepared by Cope rearrangement of a divinylcyclopropane derivative. Three functional groups on the skeleton were constructed by Barton decarboxylation, Wittig reaction, and alkylation.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>17020327</pmid><doi>10.1021/ol061947u</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2006-10, Vol.8 (21), p.4883-4885 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68933646 |
| source | MEDLINE; ACS Publications |
| subjects | Animals Anthozoa - chemistry Japan Molecular Structure Prostaglandins - chemical synthesis Prostaglandins - chemistry Stereoisomerism |
| title | Total Synthesis of (±)-Clavubicyclone |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-25T14%3A12%3A52IST&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%20of%20(%C2%B1)-Clavubicyclone&rft.jtitle=Organic%20letters&rft.au=Ito,%20Hisanaka&rft.date=2006-10-12&rft.volume=8&rft.issue=21&rft.spage=4883&rft.epage=4885&rft.pages=4883-4885&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol061947u&rft_dat=%3Cproquest_cross%3E68933646%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=68933646&rft_id=info:pmid/17020327&rfr_iscdi=true |