Assembly of a Key Dienic Intermediate for Tetrodotoxin via a Machetti-DeSarlo Reaction

作者:Chau Jaclyn; Xu Sanjia; Ciufolini Marco A*
来源:Journal of Organic Chemistry, 2013, 78(23): 11901-11910.
DOI:10.1021/jo401960p

摘要

A route to a racemic diene intermediate for the synthesis of tetrodotoxin is described. Key steps of the sequence leading to such a compound include the oxidative amidation of a phenol, a Cu(II)-catalyzed cyclocondensation of a nitroketone with an olefin (Machetti-DeSarlo reaction), and a nucleophilic fragmentation of the resulting isoxazoline. Several unusual reactions encountered in the course of this study are thoroughly discussed.

  • 出版日期2013-12-6

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