Oxidative Amidation of Phenols through the Use of Hypervalent Iodine Reagents: Development and Applications

Marco A. Ciufolini; Norbert A. Braun; Sylvain Canesi; Malika Ousmer; Jonah Chang; David Chai

doi:10.1055/s-2007-990906

REVIEW

Oxidative Amidation of Phenols through the Use of Hypervalent Iodine Reagents: Development and Applications

Marco A. Ciufolini*^a,b, Norbert A. Braun^b, Sylvain Canesi^b, Malika Ousmer^b, Jonah Chang^a, David Chai^a
^a Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada
^b Laboratoire de Synthèse et Méthodologie Organiques, CNRS UMR 5181, Université Claude Bernard Lyon 1 and Ecole Supérieure de Chimie, Physique, Electronique de Lyon, 43 bd. du 11 Novembre 1918, 69622 Villeurbanne, France
Fax: +1(604)8228710; e-Mail: ciufi@chem.ubc.ca;

Abstract

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Abstract

This contribution reviews a family of reactions devised in our laboratory that effect the oxidative conversion of phenols into 4-amido-dienones. A salient feature of this chemistry is the use of hypervalent iodine reagents, especially diacetoxyiodobenzene (DIB), as uniquely capable oxidants in the context of the new transformation. The advent of this methodology has created new opportunities in alkaloid synthesis. Our efforts toward FR-901483, TAN-1251C, cylindricine C, and other nitrogenous natural products illustrate some applications in that domain.

1 Introduction

2 Background

3 First-Generation Oxidative Amidation of Phenols: The Oxazoline Route

4 Initial Applications: Total Synthesis of FR-901483 and of TAN-1251C

5 Second-Generation Oxidative Amidation of Phenols: Sulfonamide Technology

6 Applications: Total Synthesis of (-)-Cylindricine C

7 Third-Generation Solution: The Bimolecular Reaction

8 Conclusion

Key words

phenols - amides - oxidation - hypervalent iodine - alkaloids

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Referenzen

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