Asymmetric total synthesis of prostaglandin C 2 TBS ether.
Xiaofen YiXueyu LongYu ChenXiangling CenPei TangXiangtao ChenPublished in: Chemical communications (Cambridge, England) (2022)
We disclose an asymmetric total synthesis of prostaglandin C 2 TBS ether, a derivative of an extremely sensitive natural prostaglandin C 2 . The key to the synthesis is a SmI 2 -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.