Reactivity of (3-Methylpentadienyl)iron(1+) Cation: Late-stage Introduction of a (3-Methyl-2Z,4-pentadien-1-yl) Side Chain

Abstract

Abstract:The 3-methyl-2Z,4-pentadien-1-yl sidechain is found in various sesquiterpenes and diterpenes. A route for the late stage introduction of this functionality was developed which relies on nucleophilic attack on the (3-methylpentadienyl)iron(1+) cation, followed by oxidative decomplexation. This methodology was applied to the synthesis of the proposed structure of heteroscyphic acid A methyl ester. Realization of this synthesis led to a correction of the proposed structure.