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

TitleAssembly of a Key Dienic Intermediate for Tetrodotoxin via a Machetti-DeSarlo Reaction
Publication TypeJournal Article
Year of Publication2013
AuthorsChau, J, Xu, S, Ciufolini, MA
JournalJOURNAL OF ORGANIC CHEMISTRY
Volume78
Pagination11901-11910
Date PublishedDEC 6
ISSN0022-3263
Abstract

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.

DOI10.1021/jo401960p