Asymmetric total synthesis of prostaglandin C2 TBS ether

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 stereochemic...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-05, Vol.58 (40), p.6000-6003
Main Authors: Yi, Xiaofen, Long, Xueyu, Chen, Yu, Cen, Xiangling, Tang, Pei, Chen, Fener
Format: Article
Language:English
Subjects:
Access control
Asymmetry
Dehydration
Metathesis
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc01737g