First total synthesis of (±)-epocarbazolin A and epocarbazolin B, and asymmetric synthesis of (−)-epocarbazolin A via Shi epoxidation

Epoxidation of the trisilyl-protected carbazomadurins A and B with dimethyldioxirane followed by desilylation provides a simple route to racemic epocarbazolin A and a non-diastereoselective access to epocarbazolin B. The Shi epoxidation has been applied to an asymmetric synthesis of the non-natural (−)-epocarbazolin A.

Epoxidation of the trisilyl-protected carbazomadurins A and B with dimethyldioxirane followed by desilylation provides racemic epocarbazolin A and epocarbazolin B. The Shi epoxidation has been applied to an asymmetric synthesis of (−)-epocarbazolin A.