Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin A: application of a gold-catalyzed cyclization
A new approach to total syntheses of piperidine alkaloids (+)-241D, isosolenopsin and isosolenopsin A has been developed from D-alanine. The key step to access the chiral pyridinone intermediate was achieved via a gold mediated cyclization. Finally, various reduction conditions afforded the natural...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2012-08, Vol.10 (29), p.5541-5546 |
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| container_issue | 29 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Gouault, Nicolas Le Roch, Myriam Pinto, Gisele de Campos David, Michèle |
| description | A new approach to total syntheses of piperidine alkaloids (+)-241D, isosolenopsin and isosolenopsin A has been developed from D-alanine. The key step to access the chiral pyridinone intermediate was achieved via a gold mediated cyclization. Finally, various reduction conditions afforded the natural products in few steps and good overall yields. |
| doi_str_mv | 10.1039/c2ob25685a |
| format | Article |
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The key step to access the chiral pyridinone intermediate was achieved via a gold mediated cyclization. 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Finally, various reduction conditions afforded the natural products in few steps and good overall yields.</description><subject>Alanine</subject><subject>Alanine - chemistry</subject><subject>Alkaloids</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Biochemistry</subject><subject>Biochemistry, Molecular Biology</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Gold</subject><subject>Gold - chemistry</subject><subject>Life Sciences</subject><subject>Piperidines</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Pyridones</subject><subject>Pyridones - chemistry</subject><subject>Stereoisomerism</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkctOwzAQRS0EgvLY8AHIyxYI-JHYMbuKt1SJDayjie2AwY1DnCK1G36dlEKRmM2M7hydzUXokJIzSrg61yyULBN5BhtoQFMpE5Jxtbm-GdlBuzG-EkKVFOk22mFMUpILOkCfj6EDj-O87l5sdBGHChtbmzaU0FkM_g18cAYPT0YJS-nVKXYxxOBtHZroagy1-ZeMLzA0jXcaOhfqpQ_wc_Am6QPw84U1WM-1d4vv_z7aqsBHe_Cz99DTzfXj5V0yebi9vxxPEs1z2SWKGc4slEoaAarKJEuFzIQguh8uiRZKSW5AapuavLKa5lkFZal4KVJONN9Do5X3BXzRtG4K7bwI4Iq78aRYZoTkKe2dH7Rnhyu2acP7zMaumLqorfdQ2zCLBSWMZ5znadajxytUtyHG1lZrNyXFspzir5wePvrxzsqpNWv0tw3-Bd16irU</recordid><startdate>20120807</startdate><enddate>20120807</enddate><creator>Gouault, Nicolas</creator><creator>Le Roch, Myriam</creator><creator>Pinto, Gisele de Campos</creator><creator>David, Michèle</creator><general>Royal Society of Chemistry</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><scope>1XC</scope></search><sort><creationdate>20120807</creationdate><title>Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin A: application of a gold-catalyzed cyclization</title><author>Gouault, Nicolas ; Le Roch, Myriam ; Pinto, Gisele de Campos ; David, Michèle</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c387t-92d32eab97d6a9f5724675660cccc370c69973da7ce4d8fec185fabb93b6430c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alanine</topic><topic>Alanine - chemistry</topic><topic>Alkaloids</topic><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Biochemistry</topic><topic>Biochemistry, Molecular Biology</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Gold</topic><topic>Gold - chemistry</topic><topic>Life Sciences</topic><topic>Piperidines</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Pyridones</topic><topic>Pyridones - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gouault, Nicolas</creatorcontrib><creatorcontrib>Le Roch, Myriam</creatorcontrib><creatorcontrib>Pinto, Gisele de Campos</creatorcontrib><creatorcontrib>David, Michèle</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><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gouault, Nicolas</au><au>Le Roch, Myriam</au><au>Pinto, Gisele de Campos</au><au>David, Michèle</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin A: application of a gold-catalyzed cyclization</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2012-08-07</date><risdate>2012</risdate><volume>10</volume><issue>29</issue><spage>5541</spage><epage>5546</epage><pages>5541-5546</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A new approach to total syntheses of piperidine alkaloids (+)-241D, isosolenopsin and isosolenopsin A has been developed from D-alanine. 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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2012-08, Vol.10 (29), p.5541-5546 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alanine Alanine - chemistry Alkaloids Alkaloids - chemical synthesis Alkaloids - chemistry Biochemistry Biochemistry, Molecular Biology Catalysis Cyclization Gold Gold - chemistry Life Sciences Piperidines Piperidines - chemical synthesis Piperidines - chemistry Pyridones Pyridones - chemistry Stereoisomerism |
| title | Total synthesis of dendrobate alkaloid (+)-241D, isosolenopsin and isosolenopsin A: application of a gold-catalyzed cyclization |
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