Total synthesis of epothilones B and D: Stannane equivalents for β-keto ester dianions

GE Keck, RL Giles, VJ Cee, CA Wager…

Index: Keck, Gary E.; Giles, Robert L.; Cee, Victor J.; Wager, Carrie A.; Yu, Tao; Kraft, Matthew B. Journal of Organic Chemistry, 2008 , vol. 73, # 24 p. 9675 - 9691

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Citation Number: 34

Abstract

Studies leading to a total synthesis of epothilones B and D are described. The overall synthetic plan was based on late-stage fragment assembly of two segments representing C1− C9 and C10− C21 of the structure. The C1− C9 fragment was prepared by elaboration of commercially available (2 R)-3-hydroxy-2-methylpropanoate at both ends of the three- carbon unit. Introduction of carbons 1− 4 containing the gem-dimethyl unit was achieved ...

~71%

~65%

~79%

~89%

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