Total Synthesis of (+)-Condylocarpine, (+)-Isocondylocarpine, and (+)-Tubotaiwine
The first enantioselective total syntheses of indole alkaloids of the condylocarpine type are reported. (+)-Condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine were prepared in high enantiomeric purity (er > 99:1) from (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one 7b by way...
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| Veröffentlicht in: | Organic letters 2011-01, Vol.13 (1), p.138-141 |
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| container_title | Organic letters |
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| creator | Martin, Connor L Nakamura, Seiichi Otte, Ralf Overman, Larry E |
| description | The first enantioselective total syntheses of indole alkaloids of the condylocarpine type are reported. (+)-Condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine were prepared in high enantiomeric purity (er > 99:1) from (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one 7b by way of five or six isolated intermediates. |
| doi_str_mv | 10.1021/ol102709s |
| format | Article |
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Lett</addtitle><description>The first enantioselective total syntheses of indole alkaloids of the condylocarpine type are reported. (+)-Condylocarpine, (+)-isocondylocarpine, and (+)-tubotaiwine were prepared in high enantiomeric purity (er > 99:1) from (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one 7b by way of five or six isolated intermediates.</description><subject>Alkaloids - chemical synthesis</subject><subject>Indole Alkaloids - chemical synthesis</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkdtKw0AQhhdRrFYvfAHpjWjR6B6z3RtBiodCQcR6vUw2G5uSZms2Ufr2rm0NKl7N8M_HPyeEjgi-JJiSK1eEILHyW2iPCMoiiQXdbvMYd9C-9zOMSVDULupQQhhjSu2hp4mroeg9L8t6an3uey7rnZ33o6Er02XhDFSLvLQXK23knfkjQ5muSpMmCT75RxAP0E4GhbeHm9hFL3e3k-FDNH68Hw1vxhFwieuI0EQIUCK2iRwwTGnMGEjBGZdA45QRyBgGBkZkNAHLFDOcy5hwldDMGMm66Hrtu2iSuU2NLesKCr2o8jlUS-0g178rZT7Vr-5dM0w4D-t30enGoHJvjfW1nufe2KKA0rrG6wGlTCilSCD7a9JUzvvKZm0XgvXXB3T7gcAe_xyrJb9PHoCTNQDG65lrqjJc6R-jT3Qni7A</recordid><startdate>20110107</startdate><enddate>20110107</enddate><creator>Martin, Connor L</creator><creator>Nakamura, Seiichi</creator><creator>Otte, Ralf</creator><creator>Overman, Larry E</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><scope>5PM</scope></search><sort><creationdate>20110107</creationdate><title>Total Synthesis of (+)-Condylocarpine, (+)-Isocondylocarpine, and (+)-Tubotaiwine</title><author>Martin, Connor L ; Nakamura, Seiichi ; Otte, Ralf ; Overman, Larry E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a470t-12b55a956eb783022633a754347a26d31af30a3ac5f2bae393c4476149b2fcc73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alkaloids - chemical synthesis</topic><topic>Indole Alkaloids - chemical synthesis</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Martin, Connor L</creatorcontrib><creatorcontrib>Nakamura, Seiichi</creatorcontrib><creatorcontrib>Otte, Ralf</creatorcontrib><creatorcontrib>Overman, Larry E</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>PubMed Central (Full Participant titles)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Martin, Connor L</au><au>Nakamura, Seiichi</au><au>Otte, Ralf</au><au>Overman, Larry E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of (+)-Condylocarpine, (+)-Isocondylocarpine, and (+)-Tubotaiwine</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| ispartof | Organic letters, 2011-01, Vol.13 (1), p.138-141 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkaloids - chemical synthesis Indole Alkaloids - chemical synthesis Molecular Structure Stereoisomerism |
| title | Total Synthesis of (+)-Condylocarpine, (+)-Isocondylocarpine, and (+)-Tubotaiwine |
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