Total Synthesis of (−)-Incarvilline, (+)-Incarvine C, and (−)-Incarvillateine
The first total syntheses of new monoterpene alkaloids (−)-incarvilline, (+)-incarvine C, and (−)-incarvillateine, corresponding to the natural enantiomers, have been accomplished. The strategy for the synthesis of these natural products utilized 6-epi-incarvilline as a common precursor, which was a...
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| Veröffentlicht in: | Journal of the American Chemical Society 2004-12, Vol.126 (50), p.16553-16558 |
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| container_end_page | 16558 |
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| container_issue | 50 |
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| container_title | Journal of the American Chemical Society |
| container_volume | 126 |
| creator | Ichikawa, Masaya Takahashi, Masaki Aoyagi, Sakae Kibayashi, Chihiro |
| description | The first total syntheses of new monoterpene alkaloids (−)-incarvilline, (+)-incarvine C, and (−)-incarvillateine, corresponding to the natural enantiomers, have been accomplished. The strategy for the synthesis of these natural products utilized 6-epi-incarvilline as a common precursor, which was assembled by a three-component coupling reaction using (4S)-4-siloxy-2-cyclopenten-1-one to construct an appropriately trisubstituted cyclopentanone, followed by ring closure to the cis-perhydro-2-pyrindine skeleton by means of a reductive Heck-type reaction. Furthermore, topochemically controlled [2 + 2] photodimerization of cinnamic acid derivatives in the solid state for the stereospecific construction of a 1,2,3,4-tetrasubstituted cyclobutane ring was also investigated as a means to access (−)-incarvillateine. |
| doi_str_mv | 10.1021/ja0401702 |
| format | Article |
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Furthermore, topochemically controlled [2 + 2] photodimerization of cinnamic acid derivatives in the solid state for the stereospecific construction of a 1,2,3,4-tetrasubstituted cyclobutane ring was also investigated as a means to access (−)-incarvillateine.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja0401702</identifier><identifier>PMID: 15600360</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids ; Alkaloids - chemical synthesis ; Chemistry ; Coumaric Acids - chemistry ; Crystallography, X-Ray ; Exact sciences and technology ; Magnoliopsida - chemistry ; Models, Molecular ; Monoterpenes - chemical synthesis ; Organic chemistry ; Preparations and properties ; Stereoisomerism ; Terpenoids</subject><ispartof>Journal of the American Chemical Society, 2004-12, Vol.126 (50), p.16553-16558</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-41ac4729ed359bfc10702bf7210316707964c914c9e7cb716f7cd5f1b9a2a1663</citedby><cites>FETCH-LOGICAL-a447t-41ac4729ed359bfc10702bf7210316707964c914c9e7cb716f7cd5f1b9a2a1663</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/ja0401702$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja0401702$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16370973$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15600360$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ichikawa, Masaya</creatorcontrib><creatorcontrib>Takahashi, Masaki</creatorcontrib><creatorcontrib>Aoyagi, Sakae</creatorcontrib><creatorcontrib>Kibayashi, Chihiro</creatorcontrib><title>Total Synthesis of (−)-Incarvilline, (+)-Incarvine C, and (−)-Incarvillateine</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>The first total syntheses of new monoterpene alkaloids (−)-incarvilline, (+)-incarvine C, and (−)-incarvillateine, corresponding to the natural enantiomers, have been accomplished. The strategy for the synthesis of these natural products utilized 6-epi-incarvilline as a common precursor, which was assembled by a three-component coupling reaction using (4S)-4-siloxy-2-cyclopenten-1-one to construct an appropriately trisubstituted cyclopentanone, followed by ring closure to the cis-perhydro-2-pyrindine skeleton by means of a reductive Heck-type reaction. Furthermore, topochemically controlled [2 + 2] photodimerization of cinnamic acid derivatives in the solid state for the stereospecific construction of a 1,2,3,4-tetrasubstituted cyclobutane ring was also investigated as a means to access (−)-incarvillateine.</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Alkaloids - chemical synthesis</subject><subject>Chemistry</subject><subject>Coumaric Acids - chemistry</subject><subject>Crystallography, X-Ray</subject><subject>Exact sciences and technology</subject><subject>Magnoliopsida - chemistry</subject><subject>Models, Molecular</subject><subject>Monoterpenes - chemical synthesis</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><subject>Terpenoids</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0N9KwzAUBvAgipvTC19AeqNsuOo5aZu0lzr8M5iobHob0izFzq6dSSfuDbz2EX0SIxsbiBchJOfH4eMj5BDhDIHi-URCCMiBbpEmRhT8CCnbJk0AoD6PWdAge9ZO3DOkMe6SBkYMIGDQJI-jqpaFN1yU9Yu2ufWqzGt_f351_H6ppHnPiyIvdddrn65_Su31up4sx3-hrLUb7pOdTBZWH6zuFnm6vhr1bv3B_U2_dzHwZRjy2g9RqpDTRI-DKEkzheDypxmnCAEyDjxhoUrQHc1VypFlXI2jDNNEUomMBS1ystw7M9XbXNtaTHOrtItR6mpuBeMYx5CAg50lVKay1uhMzEw-lWYhEMRvf2Ldn7NHq6XzdKrHG7kqzIHjFZBWySIzslS53TgWcEh44Jy_dLmt9cd6Ls2rCxbwSIwehuISB8-D4d1IsM1eqayYVHNTuu7-CfgDrq2QcQ</recordid><startdate>20041222</startdate><enddate>20041222</enddate><creator>Ichikawa, Masaya</creator><creator>Takahashi, Masaki</creator><creator>Aoyagi, Sakae</creator><creator>Kibayashi, Chihiro</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20041222</creationdate><title>Total Synthesis of (−)-Incarvilline, (+)-Incarvine C, and (−)-Incarvillateine</title><author>Ichikawa, Masaya ; Takahashi, Masaki ; Aoyagi, Sakae ; Kibayashi, Chihiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-41ac4729ed359bfc10702bf7210316707964c914c9e7cb716f7cd5f1b9a2a1663</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Alkaloids - chemical synthesis</topic><topic>Chemistry</topic><topic>Coumaric Acids - chemistry</topic><topic>Crystallography, X-Ray</topic><topic>Exact sciences and technology</topic><topic>Magnoliopsida - chemistry</topic><topic>Models, Molecular</topic><topic>Monoterpenes - chemical synthesis</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><topic>Terpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ichikawa, Masaya</creatorcontrib><creatorcontrib>Takahashi, Masaki</creatorcontrib><creatorcontrib>Aoyagi, Sakae</creatorcontrib><creatorcontrib>Kibayashi, Chihiro</creatorcontrib><collection>Istex</collection><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 the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ichikawa, Masaya</au><au>Takahashi, Masaki</au><au>Aoyagi, Sakae</au><au>Kibayashi, Chihiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of (−)-Incarvilline, (+)-Incarvine C, and (−)-Incarvillateine</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2004-12-22</date><risdate>2004</risdate><volume>126</volume><issue>50</issue><spage>16553</spage><epage>16558</epage><pages>16553-16558</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>The first total syntheses of new monoterpene alkaloids (−)-incarvilline, (+)-incarvine C, and (−)-incarvillateine, corresponding to the natural enantiomers, have been accomplished. The strategy for the synthesis of these natural products utilized 6-epi-incarvilline as a common precursor, which was assembled by a three-component coupling reaction using (4S)-4-siloxy-2-cyclopenten-1-one to construct an appropriately trisubstituted cyclopentanone, followed by ring closure to the cis-perhydro-2-pyrindine skeleton by means of a reductive Heck-type reaction. 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| ispartof | Journal of the American Chemical Society, 2004-12, Vol.126 (50), p.16553-16558 |
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| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Alkaloids - chemical synthesis Chemistry Coumaric Acids - chemistry Crystallography, X-Ray Exact sciences and technology Magnoliopsida - chemistry Models, Molecular Monoterpenes - chemical synthesis Organic chemistry Preparations and properties Stereoisomerism Terpenoids |
| title | Total Synthesis of (−)-Incarvilline, (+)-Incarvine C, and (−)-Incarvillateine |
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