Asymmetric Total Synthesis of Stagonolide F

Abstract

A highly convergent stereoselective total synthesis of stagonolide F is described starting from commercially available 5-hexen 1-ol using asymmetric dihydroxylation, Jacobsen^'s hydrolytic kinetic resolution (HKR), regioselective epoxide ring opening with vinyl Grignard reaction, esterification, and ring-closing metathesis (RCM) as key steps.

GRAPHICAL ABSTRACT

Keywords:

• Asymmetric dihydroxylation
• Jacobsen's hydrolytic kinetic resolution (HKR)
• ring-closing metathesis (RCM)

ACKNOWLEDGMENT

The authors thank the director, Council of Scientific and Industrial Research–Indian Institute of Chemical Technology (IICT), for her encouragement.