Synthesis of a common advanced indane intermediate for the formal total synthesis of (±)-puraquinonic acid, (±)-deliquinone, and (±)-russujaponol

Abstract

Herein we describe an efficient synthetic route to an advanced indane intermediate in four steps from 4-hydroxy-6-methyl-1-indanone which itself is synthesized from m-cresol in five steps. This constitutes formal total synthesis of all three natural products (±)-Puraquinonic Acid, (±)-Deliquinone, and (±)-Russujaponol. The operationally simple synthesis employs reactions involving methylation of phenolic indanone, β-ketoester synthesis, methylation of β-ketoester and complete reduction of benzylic carbonyl of the indanone.