The structure of fissinolide and angustidienolide, limonoids from species of meliaceae

Abstract

A recent paper has proposed revising the structure of fissinolide from methyl 3β-acetoxy-1-oxomeliac-8(14)-enate (1a) to methyl 3β-acetoxy-1-oxomeliac-8-enate (2a). Reasons are now presented for preferring the original formula. With N-bromosuccinimide, fissinolide gives the conjugated dienes methyl 3β-acetoxy-1-oxomeliac-8,14-dienate (5a) and angustidienolide. The latter is shown to be methyl 3β-acetoxy-1-oxomeliaca-8(30),14-dienate (6a).