Asymmetric synthesis of (-)-dehydroclausenamide

Article abstract of DOI:10.1016/S0040-4020(01)85453-3

Asymmetric synthesis of (-)-dehydroclausenamide 1 by scheme 2 was reported. Sharpless epoxidation was applied to cinnamyl alcohol for introduction of two desired chiral centers and the potential hydroxyl group. The key intermediate, γ-lactam (-)-5, was obtained by regio-selective intramolecular cyclization of (-)-6. Subsequent stereo-selective reduction was achieved by reducing C₃-tetrahydropyranyl ether of (-)-5. The title natural product was then obtained by successive tosylation, hydrolysis and cyclization.