Total Syntheses of (±)-Fawcettimine, (±)-Fawcettidine, (±)-Lycoflexine, and (±)-Lycoposerramine-Q
The total syntheses of four fawcettimine‐related Lycopodium alkaloids, (±)‐fawcettimine, (±)‐fawcettidine, (±)‐lycoposerramine‐Q, and (±)‐lycoflexine, were completed in a highly stereoselective manner. The Pauson–Khand reaction of 4‐methylidene‐6‐siloxyoct‐1‐en‐7‐yne followed by regio‐ and stereosel...
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| Veröffentlicht in: | Chemistry : a European journal 2013-06, Vol.19 (26), p.8665-8672 |
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| creator | Itoh, Naoya Iwata, Takashi Sugihara, Hiromi Inagaki, Fuyuhiko Mukai, Chisato |
| description | The total syntheses of four fawcettimine‐related Lycopodium alkaloids, (±)‐fawcettimine, (±)‐fawcettidine, (±)‐lycoposerramine‐Q, and (±)‐lycoflexine, were completed in a highly stereoselective manner. The Pauson–Khand reaction of 4‐methylidene‐6‐siloxyoct‐1‐en‐7‐yne followed by regio‐ and stereoselective hydrogenation led to the short‐step preparation of the bicyclo[4.3.0]nonenone intermediate bearing a methyl group with the required stereochemistry. The subsequent chemical manipulation of the bicyclic compound afforded the 6‐5‐9‐membered tricyclic dioxo compound, which was then transformed into the four targeted alkaloids in an alternative and more efficient fashion.
Fawcettimine alkaloids: The total syntheses of four fawcettimine‐related Lycopodium alkaloids, (±)‐fawcettimine, (±)‐fawcettidine, (±)‐lycoposerramine‐Q, and (±)‐lycoflexine, are described. The key steps in these syntheses are the Pauson–Khand reaction of 4‐methylidene‐6‐siloxyoct‐1‐en‐7‐yne followed by regio‐ and stereoselective hydrogenation to provide the bicyclo[4.3.0]nonenone intermediate bearing a methyl group with the required stereochemistry (see scheme). |
| doi_str_mv | 10.1002/chem.201300364 |
| format | Article |
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Fawcettimine alkaloids: The total syntheses of four fawcettimine‐related Lycopodium alkaloids, (±)‐fawcettimine, (±)‐fawcettidine, (±)‐lycoposerramine‐Q, and (±)‐lycoflexine, are described. The key steps in these syntheses are the Pauson–Khand reaction of 4‐methylidene‐6‐siloxyoct‐1‐en‐7‐yne followed by regio‐ and stereoselective hydrogenation to provide the bicyclo[4.3.0]nonenone intermediate bearing a methyl group with the required stereochemistry (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201300364</identifier><identifier>PMID: 23650145</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkaloids ; Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Bearing ; Chemistry ; cobalt ; Crystallography, X-Ray ; Heterocyclic Compounds, 3-Ring - chemical synthesis ; Heterocyclic Compounds, 3-Ring - chemistry ; Hydrogenation ; Lycopodium - chemistry ; Molecular Conformation ; natural products ; Stereochemistry ; Stereoisomerism ; total synthesis</subject><ispartof>Chemistry : a European journal, 2013-06, Vol.19 (26), p.8665-8672</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5104-506f3f64263b97a60aecc6b11cd39914fb113bf607361bab07134f66fba786763</citedby><cites>FETCH-LOGICAL-c5104-506f3f64263b97a60aecc6b11cd39914fb113bf607361bab07134f66fba786763</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201300364$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201300364$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23650145$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Itoh, Naoya</creatorcontrib><creatorcontrib>Iwata, Takashi</creatorcontrib><creatorcontrib>Sugihara, Hiromi</creatorcontrib><creatorcontrib>Inagaki, Fuyuhiko</creatorcontrib><creatorcontrib>Mukai, Chisato</creatorcontrib><title>Total Syntheses of (±)-Fawcettimine, (±)-Fawcettidine, (±)-Lycoflexine, and (±)-Lycoposerramine-Q</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>The total syntheses of four fawcettimine‐related Lycopodium alkaloids, (±)‐fawcettimine, (±)‐fawcettidine, (±)‐lycoposerramine‐Q, and (±)‐lycoflexine, were completed in a highly stereoselective manner. The Pauson–Khand reaction of 4‐methylidene‐6‐siloxyoct‐1‐en‐7‐yne followed by regio‐ and stereoselective hydrogenation led to the short‐step preparation of the bicyclo[4.3.0]nonenone intermediate bearing a methyl group with the required stereochemistry. The subsequent chemical manipulation of the bicyclic compound afforded the 6‐5‐9‐membered tricyclic dioxo compound, which was then transformed into the four targeted alkaloids in an alternative and more efficient fashion.
Fawcettimine alkaloids: The total syntheses of four fawcettimine‐related Lycopodium alkaloids, (±)‐fawcettimine, (±)‐fawcettidine, (±)‐lycoposerramine‐Q, and (±)‐lycoflexine, are described. The key steps in these syntheses are the Pauson–Khand reaction of 4‐methylidene‐6‐siloxyoct‐1‐en‐7‐yne followed by regio‐ and stereoselective hydrogenation to provide the bicyclo[4.3.0]nonenone intermediate bearing a methyl group with the required stereochemistry (see scheme).</description><subject>Alkaloids</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Bearing</subject><subject>Chemistry</subject><subject>cobalt</subject><subject>Crystallography, X-Ray</subject><subject>Heterocyclic Compounds, 3-Ring - chemical synthesis</subject><subject>Heterocyclic Compounds, 3-Ring - chemistry</subject><subject>Hydrogenation</subject><subject>Lycopodium - chemistry</subject><subject>Molecular Conformation</subject><subject>natural products</subject><subject>Stereochemistry</subject><subject>Stereoisomerism</subject><subject>total synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkctOGzEUhi3UClLKtssqUjdU6qTHc8bH4yWKCLRKL9zU7iyPY4uhc0ntiSCPxSvwZJ0QCG03rHz06_t_yfoYe8NhxAHSj_bS1aMUOAIgZVtswEXKE5QkXrABqEwmJFDtsFcxXgGAIsRttpMiCeCZGDB33namGp4tm-7SRReHrR_u392-Tybm2rquK-uycR_-jWZP0XRpW1-5m_vENLOndN5GF4JZ1ZOT1-ylN1V0ew_vLruYHJ6Pj5Ppt6NP44NpYgWHLBFAHj1lKWGhpCEwzloqOLczVIpnvj-x8AQSiRemAMkx80S-MDInSbjL9te789D-XrjY6bqM1lWVaVy7iJpLmUOqlITnUSSZ5wQ879F3_6FX7SI0_UfuqUygkLKnRmvKhjbG4Lyeh7I2Yak56JUrvXKlN676wtuH2UVRu9kGf5TTA2oNXJeVWz4zp8fHh1_-Hk_W3TJ27mbTNeGXJolS6B9fjzQ_naTyJ3zW3_EPBy-uVA</recordid><startdate>20130624</startdate><enddate>20130624</enddate><creator>Itoh, Naoya</creator><creator>Iwata, Takashi</creator><creator>Sugihara, Hiromi</creator><creator>Inagaki, Fuyuhiko</creator><creator>Mukai, Chisato</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20130624</creationdate><title>Total Syntheses of (±)-Fawcettimine, (±)-Fawcettidine, (±)-Lycoflexine, and (±)-Lycoposerramine-Q</title><author>Itoh, Naoya ; Iwata, Takashi ; Sugihara, Hiromi ; Inagaki, Fuyuhiko ; Mukai, Chisato</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5104-506f3f64263b97a60aecc6b11cd39914fb113bf607361bab07134f66fba786763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkaloids</topic><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Bearing</topic><topic>Chemistry</topic><topic>cobalt</topic><topic>Crystallography, X-Ray</topic><topic>Heterocyclic Compounds, 3-Ring - chemical synthesis</topic><topic>Heterocyclic Compounds, 3-Ring - chemistry</topic><topic>Hydrogenation</topic><topic>Lycopodium - chemistry</topic><topic>Molecular Conformation</topic><topic>natural products</topic><topic>Stereochemistry</topic><topic>Stereoisomerism</topic><topic>total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Itoh, Naoya</creatorcontrib><creatorcontrib>Iwata, Takashi</creatorcontrib><creatorcontrib>Sugihara, Hiromi</creatorcontrib><creatorcontrib>Inagaki, Fuyuhiko</creatorcontrib><creatorcontrib>Mukai, Chisato</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Itoh, Naoya</au><au>Iwata, Takashi</au><au>Sugihara, Hiromi</au><au>Inagaki, Fuyuhiko</au><au>Mukai, Chisato</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Syntheses of (±)-Fawcettimine, (±)-Fawcettidine, (±)-Lycoflexine, and (±)-Lycoposerramine-Q</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2013-06-24</date><risdate>2013</risdate><volume>19</volume><issue>26</issue><spage>8665</spage><epage>8672</epage><pages>8665-8672</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>The total syntheses of four fawcettimine‐related Lycopodium alkaloids, (±)‐fawcettimine, (±)‐fawcettidine, (±)‐lycoposerramine‐Q, and (±)‐lycoflexine, were completed in a highly stereoselective manner. The Pauson–Khand reaction of 4‐methylidene‐6‐siloxyoct‐1‐en‐7‐yne followed by regio‐ and stereoselective hydrogenation led to the short‐step preparation of the bicyclo[4.3.0]nonenone intermediate bearing a methyl group with the required stereochemistry. The subsequent chemical manipulation of the bicyclic compound afforded the 6‐5‐9‐membered tricyclic dioxo compound, which was then transformed into the four targeted alkaloids in an alternative and more efficient fashion.
Fawcettimine alkaloids: The total syntheses of four fawcettimine‐related Lycopodium alkaloids, (±)‐fawcettimine, (±)‐fawcettidine, (±)‐lycoposerramine‐Q, and (±)‐lycoflexine, are described. The key steps in these syntheses are the Pauson–Khand reaction of 4‐methylidene‐6‐siloxyoct‐1‐en‐7‐yne followed by regio‐ and stereoselective hydrogenation to provide the bicyclo[4.3.0]nonenone intermediate bearing a methyl group with the required stereochemistry (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>23650145</pmid><doi>10.1002/chem.201300364</doi><tpages>8</tpages></addata></record> |
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| source | Wiley Online Library - AutoHoldings Journals; MEDLINE |
| subjects | Alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry Bearing Chemistry cobalt Crystallography, X-Ray Heterocyclic Compounds, 3-Ring - chemical synthesis Heterocyclic Compounds, 3-Ring - chemistry Hydrogenation Lycopodium - chemistry Molecular Conformation natural products Stereochemistry Stereoisomerism total synthesis |
| title | Total Syntheses of (±)-Fawcettimine, (±)-Fawcettidine, (±)-Lycoflexine, and (±)-Lycoposerramine-Q |
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