Practical asymmetric synthesis of hastanecine and dihydroxyheliotridane by a Claisen rearrangement/amine-epoxide-opening sequence

Article abstract of DOI:10.1055/s-1993-25913

A practical 13-step synthesis of the title compounds suitable for the gram scale has been developed. Key steps are Sharpless resolution, Claisen rearrangement, epoxidation and intramolecular S(N)2 ring closure to form the pyrrolizidine system.