Synthesis of 7,2′-Dihydroxy-4′,5′-Dimethoxyisoflavanone, a Phytoestrogen with Derma Papilla Cell Proliferative Activity

Abstract

This paper reports a concise and scalable method for the synthesis of the phytoestrogen 7,2′-dihydroxy-4′,5′-dimethoxyisoflavanone 1 via an optimized synthetic route. Compound 1 was readily obtained in 11 steps and 11% overall yield on a gram scale from commercially available 3,4-dimethoxyphenol. The key features of the synthesis include the construction of the deoxybenzoin unit through a sequence of Claisen rearrangement, oxidative cleavage, and aryllithium addition and the efficient synthesis of the isoflavanone architecture from highly functionalized 2-hydroxyketone.

Synthesis of deoxybenzoins from β-alkoxy styrenes and arylboronic acids via palladium-catalyzed regioselective Heck-arylation reactions

“…Deoxybenzoins ( also known as α-aryl acetophenones) are important scaffolds in chemistry and biology. 1 They are part of different natural products and drug molecules (Fig. 1).…”