Synthesis of sphingosine relatives. Part VI. Stereocontrolled synthesis of (2R,3R,5R,13S,14R)-(+)-aplisiasphingosine, a marine terpenoid.

DOI 2 Citations
  • UMEMURA Takeaki
    Department of Agricultural Chemistry, The University of Tokyo Present address: Takarazuka Research Center, Sumitomo Chemical Co.
  • MORI Kenji
    Department of Agricultural Chemistry, The University of Tokyo

Abstract

The Sharpless asymmetric epoxidation was used for the synthesis of both D-erythro-dihydrosphingosine triacetate and (2S, 3S, 5R)-2-acetamino-5, 9-dimethyl-8-decene-1, 3-diol. A 13C-NMR study of the latter coupled with biogenetic considerations enabled us to propose (2R*, 3R*, 5R*, 13S*, 14R*)-relative stereochemistry for natural aplidiasphingosine. (2R, 3R, 5R, 13R, 14R)-(+)-aplidiasphingosine was synthesised starting from (R)-(+)-citronellic acid.

Journal

Citations (2)*help

See more

Keywords

Details 詳細情報について

  • CRID
    1390001206463068672
  • NII Article ID
    130000025001
  • DOI
    10.1271/bbb1961.51.1973
  • COI
    1:CAS:528:DyaL1cXitVCrtro%3D
  • ISSN
    18811280
    00021369
    http://id.crossref.org/issn/00021369
  • Text Lang
    en
  • Data Source
    • JaLC
    • Crossref
    • CiNii Articles
  • Abstract License Flag
    Disallowed

Report a problem

Back to top