Allylic oxidations in natural product synthesis

Akihiko Nakamura, Masahisa Nakada

Research output: Contribution to journalReview article

71 Citations (Scopus)

Abstract

Although C-H oxidation of hydrocarbons is generally difficult, allylic C-H oxidation is relatively simple and predictable, even on a preparative scale, because active species generated at the allylic position are stabilized by the double bond. Therefore, allylic oxidation has been employed in natural product synthesis, and a variety of reagents and conditions for allylic oxidation have been reported. However, reagents and conditions suitable for natural product synthesis are limited in terms of efficiency and chemo-, regio-, and stereoselectivity, owing to the structural and characteristic diversity of natural products. This review addresses allylic oxidations, highlighting reagents and conditions that meet the requirements for natural product synthesis. 1 Introduction 2 Selenium Reagents 2.1 Selenium Dioxide 2.2 Diphenyldiselenide-Iodoxybenzene 3 Chromium(VI) Reagents 3.1 Chromic Acid and Chromate Ester 3.2 Chromium Trioxide-3,5-Dimethylpyrazole (CrO 3·3,5-DMP) 3.3 PCC and PDC 4 Transition-Metal Reagents 5 Others 6 Conclusion.

Original languageEnglish
Article numberSS-2012-E0997-R
Pages (from-to)1421-1451
Number of pages31
JournalSynthesis (Germany)
Volume45
Issue number11
DOIs
Publication statusPublished - 2013 May 15

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Keywords

  • C-H oxidation
  • allylic oxidation
  • natural products
  • selectivity
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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