Intramolecular Diels-Alder Cycloaddition Approach toward the cis-Fused Delta(5,6)-Hexahydroisoindol-1-one Core of Cytochalasins

摘要

Synthesis of the cis-fused Delta(5,6)-hexahydroisoindol-1-one core of cytochalasins B-2-B-5, K, Z(8), Z(9), Z(12)-Z(15), and Z(17) has been established starting from an intramolecular Diels-Alder reaction of the amide-tethered (8E)-1,3,8-nonatriene. The transfused 5/6-bicyclic adduct was then subjected to highly stereo selective C9-beta-hydroxylation and epimerization of the C7-alpha-OH group.