Stereocontrolled Functionalization of Cycloheptadiene by Nucleophile Addition to Cycloheptadienyliron Complexes - Preparation and Reactions of 6-Methylcyclohepta-2,4-dienol Derivatives

Abstract

Addition of alkoxide nucleophiles to methyl-substituted cycloheptadienyliron complex (6) proceeds with complete stereo-and regio-selectivity. The product cycloheptadiene complexes are readily demetallated to give cycloheptadienes that can be further functionalized to give potential building blocks for the synthesis of macrolide antibiotics. Stereocontrolled reduction of the keto derivative (26) allows access to a stereochemically complementary cycloheptadiene. Functionalization of the diene moiety of these compounds is described.