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Tandem Phenolic Oxidative Amidation-Intramolecular Diels-Alder Reaction: An Approach to the Himandrine Core.

TitleTandem Phenolic Oxidative Amidation-Intramolecular Diels-Alder Reaction: An Approach to the Himandrine Core.
Publication TypeJournal Article
Year of Publication2010
AuthorsLiang, H, Ciufolini, MA
JournalOrganic Letters
Volume12
Pagination1760 - 1763
Date Published2010///
ISBN Number1523-7060
Keywordsphenolic oxidative amidation intramol Diels Alder himandrine intermediate
Abstract

An oxidative cyclization of dienic sulfonamides, e.g. I, mediated by iodobenzene diacetate in TFA, followed by a tandem intramol. Diels-Alder reaction, achieves desymmetrization of a "locally sym." dienone with good levels of diastereoselectivity and leads to valuable synthetic intermediates for the himandrine alkaloids, e.g. II. [on SciFinder(R)]