Studies on reductive alkylation. A highly efficient synthesis of the phytoalexin orchinol

Abstract

Reductive alkylation of 2,5-dimethoxybenzoic acid (1) with 2-(3',5'-dimethoxyphenyl)ethyl iodide (2) followed by cyclodehydration and oxidative decarboxylation afforded orchinol (5) in high overallyield. A simple synthesis of iodide (2) based on the reductive alkylation of 3,5-dimethoxybenzoic acid (6) was also developed.