A PhSeCl-Mediated Allylic Oxidation of Prenyl Moiety : A Convenient Method for the Construction of 3-Isopenten-2-ol Unit

    • OSHIDA Motoko
    • Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)
    • NAKAMURA Tomoaki
    • Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)
    • NAKAZAKI Atsuo
    • Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)
    • KOBAYASHI Susumu
    • Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI)

Abstract

A phenylselenenyl chloride (PhSeCl)-mediated allylic oxidation to give allylically rearranged alcohol has been developed. A possible mechanism for the present reaction is generation of allylic selenide from prenyl moiety via [1,3]-sigmatropic rearrangement, followed by oxidation and [2,3]-sigmatropic rearrangement to afford 3-isopenten-2-ol.

Journal

Chemical & pharmaceutical bulletin   [List of Volumes]

Chemical & pharmaceutical bulletin 56(3), 404-406, 2008-03-01  [Table of Contents]

The Pharmaceutical Society of Japan

References:  14

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Codes

  • NII Article ID (NAID) :
    110006622652
  • NII NACSIS-CAT ID (NCID) :
    AA00602100
  • Text Lang :
    ENG
  • Article Type :
    NOT
  • ISSN :
    00092363
  • NDL Article ID :
    9394916
  • NDL Source Classification :
    ZS51(科学技術--薬学) // ZP1(科学技術--化学・化学工業)
  • NDL Call No. :
    Z53-D167
  • DOI :
    10.1248/cpb.56.404
  • Databases :
    CJP  NDL  NII-ELS  J-STAGE