Transesterification of a Natural Epoxythymol Is Favored under Alkaline Conditions, Preserving the Enantiomeric Purity

Abstract

Transesterification is a synthetic chemistry strategy promoted in acid or alkaline conditions, yielding a structural diversity of organic compounds. Epoxythymols comprise a class of chiral natural compounds with biological relevance, and the literature describes their chiral purity loss during acid transesterification reactions. This work reports the basic transesterification of the natural derivative (8S)-10-benzoylxy-8,9-epoxy-6-hydroxythymol under alkaline conditions. Herein, the formation of (8S)-10-benzoylxy-6-isobutyryloxy-8,9-epoxythymol isobutyrate is gained, avoiding the loss of optical purity. 1H NMR-BINOL experiments revealed the enantiomeric purity of the product reaction. These results highlight that the implemented strategy promotes transesterification, preserving optical purity.

Keywords

• epoxythymol
• transesterification
• chirality