Tetrahedron

Total synthesis of neopeltolide and analogs

Y Cui, W Tu, PE Floreancig

Index: Cui, Yubo; Tu, Wangyang; Floreancig, Paul E. Tetrahedron, 2010 , vol. 66, # 26 p. 4867 - 4873

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Citation Number: 31

Abstract

Neopeltolide, a potent cytotoxin from a Carribean sponge, was synthesized through a brief sequence that highlights the use of ethers as oxocarbenium ion precursors. Other key steps include an acid-mediated etherification and sequence that features a Sonogashira reaction, an intramolecular alkyne hydrosilylation reaction, and a Tamao oxidation. The alkene that is required for the oxidative cyclization can be hydrogenated to provide access to the natural ...

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