Efficient total syntheses of (±)-vincadifformine and (-)-tabersonine

Article abstract of DOI:10.1016/S0040-4039(98)02667-7

Stereocontrolled biomimetic total syntheses of the title compounds are described. Our syntheses feature a highly efficient preparation of the key intermediate 11 using our novel indole synthesis methodology. A novel amine protecting protocol by means of 2,4-dinitrobenzenesulfonamides has been developed to ensure the formation of the elusive secodine (3) as well as secodine-type intermediate (4) under very mild conditions.