Total Synthesis of Both Spiroketal Diastereomers of the Reported Structure of Cephalosporolide H

Abstract

Abstract A total synthesis of both spiroketal diastereomers of the reported structure of cephalosporolide H is accomplished in 12 steps and 9 % overall yield. The key steps involve Keck’s allylation, cross metathesis (to get the desired β,γ‐unsaturated ester), Sharpless asymmetric dihydroxylation (to install the β‐hydroxy‐γ‐lactone moiety), and spiroketalization to access both spiroketal diastereomers of the reported structure of the natural product.