Asymmetric total synthesis of prostaglandin C2 TBS ether. Issue 40 (29th April 2022)

• Record Type: Journal Article
• Authors: Yi, Xiaofen; Long, Xueyu; Chen, Yu; Cen, Xiangling; Tang, Pei; Chen, Fener
• Is Part Of: Chemical communications. Volume 58:Issue 40(2022)
• Page Start: 6000
• Page End: 6003
• Publication Date: 2022-04-29
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc01737g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Asymmetric total synthesis of prostaglandin C2 TBS ether has been achieved via a stereoselective SmI2 -mediated ketyl–enoate cyclization and a Grignard addition/dehydration/metathesis sequence. 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.