The first asymmetric synthesis of marliolide from readily accessible carbohydrate as chiral template

Abstract

A simple and efficient strategy for the first asymmetric total synthesis of marliolide was accomplished by using stereoselective alkylation of the dianion of the β-hydroxy lactone enolate with myristyl aldehyde as a key step. The key intermediate, β-hydroxyl γ-methyl butyrolactone was prepared by transformation of L-lyxonolactone starting from D-ribose, a naturally abundant chiral carbohydrate.

Keywords: Asymmetric synthesis; Lactone enolate alkylation; Marliolide; γ-butyrolactone.