The chemistry of pseudomonic acid. Part 10. Preparation of heterocyclic derivatives

Abstract

The preparation of a large variety of normonyl heterocycles is described. Methods involving cyclisation of monic acid derivatives gave access to only a limited number of types of heterocycles. Olefination methods proved to be of wider applicability with phosphonate stabilised anions providing the biologically active E-isomer in a 3–4 : 1 excess. The Peterson type olefination proved to be the most useful method with the largest range of heterocycles and stereoselectivity of E:Z 4 to >10 : 1.