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Synthetic ventures inspired by biosynthetic hypotheses: the evolution of a method for the oxidative amidation of phenols

TitleSynthetic ventures inspired by biosynthetic hypotheses: the evolution of a method for the oxidative amidation of phenols
Publication TypeJournal Article
Year of Publication2006
AuthorsCiufolini, MA, Canesi, S, Ousmer, M, Braun, NA
JournalTetrahedron
Volume62
Pagination5318-5337
Date PublishedMay
Type of ArticleReview
ISBN Number0040-4020
KeywordsALPHA-AMINO-ALDEHYDES, AROMATIC-SUBSTITUTION, ASCIDIAN CLAVELINA-CYLINDRICA, ELECTROPHILIC, HIGH ENANTIOMERIC EXCESS, HYPERVALENT IODINE OXIDATION, IMMUNOSUPPRESSANT FR901483, MANNICH CYCLIZATION APPROACH, MARINE ALKALOIDS, N-ACYLNITRENIUM IONS, NITROGEN HETEROCYCLIC-COMPOUNDS, POTENT, TRICYCLIC
Abstract

We describe the development of a technique for the oxidative conversion of 4-alkyl phenols to derivatives of the corresponding 4-alkyl-4-amino-2,5-cyclohexanediones. This transformation, which was inspired by biogenetic considerations, constitutes a key step in the total syntheses of FR-901483, TAN-1251C, and cylindricine C. (c) 2006 Elsevier Ltd. All rights reserved.
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