Total Synthesis of 10-Isocyano-4-cadinene and Its Stereoisomers and Evaluations of Antifouling Activities
The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, and determination of its absolute stereochemistry were achieved. 10-Isocyano-4-cadinene is expected to be a novel nontoxic antifouling agent. In the synt...
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| Veröffentlicht in: | Journal of organic chemistry 2011-08, Vol.76 (16), p.6558-6573 |
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| container_issue | 16 |
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| container_title | Journal of organic chemistry |
| container_volume | 76 |
| creator | Nishikawa, Keisuke Nakahara, Hiroshi Shirokura, Yousuke Nogata, Yasuyuki Yoshimura, Erina Umezawa, Taiki Okino, Tatsufumi Matsuda, Fuyuhiko |
| description | The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, and determination of its absolute stereochemistry were achieved. 10-Isocyano-4-cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, intermolecular Diels–Alder reaction and samarium diiodide induced Barbier-type cyclization were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined as (1S,6S,7R,10S) by comparison of the optical rotations between natural and synthetic samples. In addition, the authors successfully synthesized 10-epi- and di-1,6-epi-10-isocyano-4-cadinene through the same synthetic pathway. Antifouling activities against Balanus amphitrite with the cadinenes were also evaluated. |
| doi_str_mv | 10.1021/jo2008109 |
| format | Article |
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In the synthesis, intermolecular Diels–Alder reaction and samarium diiodide induced Barbier-type cyclization were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined as (1S,6S,7R,10S) by comparison of the optical rotations between natural and synthetic samples. In addition, the authors successfully synthesized 10-epi- and di-1,6-epi-10-isocyano-4-cadinene through the same synthetic pathway. Antifouling activities against Balanus amphitrite with the cadinenes were also evaluated.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo2008109</identifier><identifier>PMID: 21755975</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids ; Animals ; Chemistry ; Cyanides - chemical synthesis ; Cyanides - chemistry ; Cyanides - pharmacology ; Cyclization ; Exact sciences and technology ; Magnetic Resonance Spectroscopy ; Naphthalenes - chemical synthesis ; Naphthalenes - chemistry ; Naphthalenes - pharmacology ; Optical Rotation ; Organic chemistry ; Preparations and properties ; Sesquiterpenes - chemical synthesis ; Sesquiterpenes - chemistry ; Sesquiterpenes - pharmacology ; Stereoisomerism ; Terpenoids ; Thoracica - drug effects</subject><ispartof>Journal of organic chemistry, 2011-08, Vol.76 (16), p.6558-6573</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-365da717e7d41ee4a1ab8fe6a4aebfae6762c09ad0b2ca95395719d83974bcf13</citedby><cites>FETCH-LOGICAL-a410t-365da717e7d41ee4a1ab8fe6a4aebfae6762c09ad0b2ca95395719d83974bcf13</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/jo2008109$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo2008109$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24425044$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21755975$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nishikawa, Keisuke</creatorcontrib><creatorcontrib>Nakahara, Hiroshi</creatorcontrib><creatorcontrib>Shirokura, Yousuke</creatorcontrib><creatorcontrib>Nogata, Yasuyuki</creatorcontrib><creatorcontrib>Yoshimura, Erina</creatorcontrib><creatorcontrib>Umezawa, Taiki</creatorcontrib><creatorcontrib>Okino, Tatsufumi</creatorcontrib><creatorcontrib>Matsuda, Fuyuhiko</creatorcontrib><title>Total Synthesis of 10-Isocyano-4-cadinene and Its Stereoisomers and Evaluations of Antifouling Activities</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, and determination of its absolute stereochemistry were achieved. 10-Isocyano-4-cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, intermolecular Diels–Alder reaction and samarium diiodide induced Barbier-type cyclization were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined as (1S,6S,7R,10S) by comparison of the optical rotations between natural and synthetic samples. In addition, the authors successfully synthesized 10-epi- and di-1,6-epi-10-isocyano-4-cadinene through the same synthetic pathway. Antifouling activities against Balanus amphitrite with the cadinenes were also evaluated.</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Animals</subject><subject>Chemistry</subject><subject>Cyanides - chemical synthesis</subject><subject>Cyanides - chemistry</subject><subject>Cyanides - pharmacology</subject><subject>Cyclization</subject><subject>Exact sciences and technology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Naphthalenes - chemical synthesis</subject><subject>Naphthalenes - chemistry</subject><subject>Naphthalenes - pharmacology</subject><subject>Optical Rotation</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Sesquiterpenes - chemical synthesis</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Stereoisomerism</subject><subject>Terpenoids</subject><subject>Thoracica - drug effects</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1LJDEQhoO46OjuwT8gfRHx0G4lnfTHcRB3HRA86J6b6nS1RnoSTaWF-ff26qgXC4qC4qm34BHiSMK5BCV_PwYFUEtodsRCGgV52YDeFQsApfJClcW-OGB-hLmMMXtiX8nKmKYyC-HuQsIxu9349EDsOAtDJiFfcbAb9CHXucXeefKUoe-zVeLsNlGk4DisKfLb9vIFxwmTC_7tfumTG8I0On-fLW1yLy454p_ix4Aj06_tPBT__lzeXVzl1zd_VxfL6xy1hJQXpemxkhVVvZZEGiV29UAlaqRuQCqrUllosIdOWWxM0ZhKNn1dNJXu7CCLQ3H6nvsUw_NEnNq1Y0vjiJ7CxG1dFwXMrWby7J20MTBHGtqn6NYYN62E9r_Y9lPszB5vU6duTf0n-WFyBk62ALLFcYjoreMvTmtlQOsvDi3P-VP0s4xvHr4C3rmMNQ</recordid><startdate>20110819</startdate><enddate>20110819</enddate><creator>Nishikawa, Keisuke</creator><creator>Nakahara, Hiroshi</creator><creator>Shirokura, Yousuke</creator><creator>Nogata, Yasuyuki</creator><creator>Yoshimura, Erina</creator><creator>Umezawa, Taiki</creator><creator>Okino, Tatsufumi</creator><creator>Matsuda, Fuyuhiko</creator><general>American Chemical Society</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>7X8</scope></search><sort><creationdate>20110819</creationdate><title>Total Synthesis of 10-Isocyano-4-cadinene and Its Stereoisomers and Evaluations of Antifouling Activities</title><author>Nishikawa, Keisuke ; Nakahara, Hiroshi ; Shirokura, Yousuke ; Nogata, Yasuyuki ; Yoshimura, Erina ; Umezawa, Taiki ; Okino, Tatsufumi ; Matsuda, Fuyuhiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-365da717e7d41ee4a1ab8fe6a4aebfae6762c09ad0b2ca95395719d83974bcf13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Animals</topic><topic>Chemistry</topic><topic>Cyanides - chemical synthesis</topic><topic>Cyanides - chemistry</topic><topic>Cyanides - pharmacology</topic><topic>Cyclization</topic><topic>Exact sciences and technology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Naphthalenes - chemical synthesis</topic><topic>Naphthalenes - chemistry</topic><topic>Naphthalenes - pharmacology</topic><topic>Optical Rotation</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Sesquiterpenes - chemical synthesis</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Stereoisomerism</topic><topic>Terpenoids</topic><topic>Thoracica - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nishikawa, Keisuke</creatorcontrib><creatorcontrib>Nakahara, Hiroshi</creatorcontrib><creatorcontrib>Shirokura, Yousuke</creatorcontrib><creatorcontrib>Nogata, Yasuyuki</creatorcontrib><creatorcontrib>Yoshimura, Erina</creatorcontrib><creatorcontrib>Umezawa, Taiki</creatorcontrib><creatorcontrib>Okino, Tatsufumi</creatorcontrib><creatorcontrib>Matsuda, Fuyuhiko</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>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nishikawa, Keisuke</au><au>Nakahara, Hiroshi</au><au>Shirokura, Yousuke</au><au>Nogata, Yasuyuki</au><au>Yoshimura, Erina</au><au>Umezawa, Taiki</au><au>Okino, Tatsufumi</au><au>Matsuda, Fuyuhiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of 10-Isocyano-4-cadinene and Its Stereoisomers and Evaluations of Antifouling Activities</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2011-08-19</date><risdate>2011</risdate><volume>76</volume><issue>16</issue><spage>6558</spage><epage>6573</epage><pages>6558-6573</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, and determination of its absolute stereochemistry were achieved. 10-Isocyano-4-cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, intermolecular Diels–Alder reaction and samarium diiodide induced Barbier-type cyclization were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined as (1S,6S,7R,10S) by comparison of the optical rotations between natural and synthetic samples. In addition, the authors successfully synthesized 10-epi- and di-1,6-epi-10-isocyano-4-cadinene through the same synthetic pathway. Antifouling activities against Balanus amphitrite with the cadinenes were also evaluated.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>21755975</pmid><doi>10.1021/jo2008109</doi><tpages>16</tpages></addata></record> |
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| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Animals Chemistry Cyanides - chemical synthesis Cyanides - chemistry Cyanides - pharmacology Cyclization Exact sciences and technology Magnetic Resonance Spectroscopy Naphthalenes - chemical synthesis Naphthalenes - chemistry Naphthalenes - pharmacology Optical Rotation Organic chemistry Preparations and properties Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Stereoisomerism Terpenoids Thoracica - drug effects |
| title | Total Synthesis of 10-Isocyano-4-cadinene and Its Stereoisomers and Evaluations of Antifouling Activities |
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