Allylic oxidations in natural product synthesis

Akihiko Nakamura, Masahisa Nakada

    Research output: Contribution to journalArticle

    67 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

    Fingerprint

    Biological Products
    Oxidation
    Selenium
    Chromium
    Selenium Oxides
    Stereoselectivity
    Regioselectivity
    Chromates
    Transition metals
    Hydrocarbons
    Esters
    Acids

    Keywords

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

    ASJC Scopus subject areas

    • Organic Chemistry
    • Catalysis

    Cite this

    Allylic oxidations in natural product synthesis. / Nakamura, Akihiko; Nakada, Masahisa.

    In: Synthesis (Germany), Vol. 45, No. 11, SS-2012-E0997-R, 2013, p. 1421-1451.

    Research output: Contribution to journalArticle

    Nakamura, Akihiko ; Nakada, Masahisa. / Allylic oxidations in natural product synthesis. In: Synthesis (Germany). 2013 ; Vol. 45, No. 11. pp. 1421-1451.
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