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Asymmetric total synthesis of prostaglandin C2 TBS ether
Xiaofen Yi1, Xueyu Long1, Yu Chen1
1Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China. peitang@scu.edu.cn.
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.
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