Intramolecular Oxidative Coupling of Aromatic Compounds. VII. A Convenient Synthesis of (±)-Deoxyschizandrin

Abstract

A convenient synthesis of (±)-deoxyschizandrin was achieved through the key step of reductive coupling of the bisacetonylbiphenyl (3). The latter compound was synthesized by oxidative cleavage of the bis olefin (5) formed by Claisen rearrangement of the bismethallyl ether of 2,2′,4,4′-tetramethoxybiphenyl-3,3′-diol. The synthesis of 2,2′,4,4′-tetramethoxy-6,6′-di(prop 1-enyl)biphenyl-3,3′-diol (2) is also described. The diphenolic oxidation of (2) did not lead to products with β,β′ carbons linked.