Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems II: Application to asymmetric syntheses of piperidine and indolizidine alkaloids

Article abstract of DOI:10.1016/S0040-4020(99)00073-3

The asymmetric synthesis of (-)-pinidine and its enantiomer was accomplished by starting from norgranatanone via the asymmetric enolization, stereoselective cyclopropanation, and oxidative ring cleavage of the resulting cyclopropanol system with a hypervalent λ(n)-iodane as key steps. Formal asymmetric synthesis of (+)-indolizidine 223AB was also performed via the asymmetric enolization and oxidative ring cleavage of the resulting cyclopropanol system as key steps.