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Approach to Tetrodotoxin via the Oxidative Amidation of a Phenol

TitleApproach to Tetrodotoxin via the Oxidative Amidation of a Phenol
Publication TypeJournal Article
Year of Publication2009
AuthorsMendelsohn, BA, Ciufolini, MA
JournalOrganic Letters
Volume11
Pagination4736-4739
Date PublishedOct
Type of ArticleArticle
ISBN Number1523-7060
Abstract

An approach to tetrodotoxin that relies on the oxidative amidation of methyl 4-hydroxyphenylacetate as a key step is described. The stereoselective Introduction of a beta-hydroxynitrile functionality on one of the double bonds of the emerging dienone is achieved through an intramolecular nitrile oxide cycloaddition-fragmentation sequence.

DOI10.1021/ol901914u