Synthesis of (S)-γ-Lactones with a Combination of Lipase-Catalyzed Resolution and Mitsunobu Reaction

Abstract

Six kinds of (S)-γ-lactones [e.g., (S)-γ-decalactone, (S)-γ-undecalactone, and (S)-γ-jasmolactone] were synthesized with 71–88% yields and >97% optical purities by combining lipase-catalyzed resolution with the Mitsunobu reaction.

Keywords:

• Asymmetric synthesis
• enzyme
• kinetic resolution
• Mitsunobu reaction

ACKNOWLEDGMENT

We are grateful to Novozymes A/S for the generous gift of Novozym 435. Financial support from Meiji University (Grant-in-Aid for Young Scientists) is gratefully acknowledged.

Notes

^a Yield based on rac-1c.

^b Determined by GC using Chirasil-Dex CB column.

^a Yield based on rac-1c.

^b Determined by GC using Chirasil-Dex CB column.

^a Yield based on rac-1.

^b Determined by GC using Chirasil-Dex CB column.