Asymmetric total synthesis of prostaglandin C2 TBS ether

Abstract

We disclose an asymmetric total synthesis of prostaglandin C₂ TBS ether, a derivative of an extremely sensitive natural prostaglandin C₂. The key to the synthesis is a SmI₂-mediated ketyl–enoate reaction that leads to the formation of the functionalized cyclopentane ring with high-level stereochemical control. Access to the crucial alkene system is realized late in the synthesis by the implementation of a Grignard addition/dehydration/metathesis sequence.