Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis

Abstract

A concise and diastereoselective total synthesis of tetraketide and euscapholide is described in ten steps in 10.6% overall yield from acetaldehyde and (S)-pent-4-ene-1,2-diol. Jacobsen hydrolytic kinetic­ resolution, Prins cyclization, ring-closing metathesis and oxa-Michael­ addition reactions are the key steps involved in the synthesis.

Keywords

• prins cyclization
• euscapholide
• tetraketide
• ring-closing metathesis