Total Synthesis of (+)-Condylocarpine, (+)-Isocondylocarpine, and (+)-Tubotaiwine

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
Hauptverfasser: Martin, Connor L, Nakamura, Seiichi, Otte, Ralf, Overman, Larry E
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Indole Alkaloids - chemical synthesis
Molecular Structure
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102709s