Synthesis of (-)-Muricatacin

    • Makabe Hidefumi
    • Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University
    • Tanaka Akira
    • Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University
    • Oritani Takayuki
    • Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University

Abstract

The synthesis of (-)-muricatacin starting from 1-bromododecane and 2-pentyn-1-ol is described. 2-Pentadecyn-1-ol (4), which was prepared from 1-bromododecane (2) and 2-pentyn-1-ol (3), was converted to epoxy alcohol 6 through a two-step reaction sequence, 6 being successively submitted to tosylation, iodination, chain extension with tert-butyl lithioacetate, and acid-catalyzed cyclization to give (-)-muricatacin (1a). Recrystallization afforded optically pure 1a.

Journal

Bioscience, biotechnology, and biochemistry   [List of Volumes]

Bioscience, biotechnology, and biochemistry 57(6), 1028-1029, 1993-06-23  [Table of Contents]

Japan Society for Bioscience, Biotechnology, and Agrochemistry

Cited by:  4

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Codes

  • NII Article ID (NAID) :
    110002676412
  • NII NACSIS-CAT ID (NCID) :
    AA10824164
  • Text Lang :
    ENG
  • Article Type :
    Journal Article
  • ISSN :
    09168451
  • DOI :
    10.1271/bbb.57.1028
  • Databases :
    CJPref  NII-ELS  Journal@rchive 

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