A convenient synthesis method for methylenomycin B and its application to methylenomycis A.

DOI 1 Citations
  • TONARI Kennosuke
    Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture
  • MACHIYA Kozo
    Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture
  • ICHIMOTO Itsuo
    Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture
  • UEDA Hiroo
    Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture

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Description

A convenient synthesis method for methylenomycin B and its homolog, methylenomycin A, has been developed. Methylenomycin B, 2, 3-dimethyl-5-methylene-2-cyclopentenone (3) was synthesized: i) by methylation of Mannich derivative prepared from morpholine and 2, 3-dimethyl-2-cyclopentenone (5) or ii) by treatment of formalin with sodio derivatives of 2, 3-dimethyl-5-formyl-2-cyclopentenone (7a) and 2, 3-dimethyl-5-ethoxalyl-2-cyclopentenone (7b), both of which were easily prepared from 5 and ethyl formate or ethyl oxalate. 2, 3-Dimethyl-2, 3-epoxy-5- methylenecyclopentanone (2) was similarly prepared from the epoxide compound of 5 and ethyl oxalate. The bioassay of methylenomycin B and its related compounds against bacteria (B. subtilis, S. aureus, Ps. aeruginosa and E. coli) was also conducted. Methylenomycin A (1) and its desepoxy compound (17) were also prepared from 4-carboxy-2, 3-dimethyl-2-cyclopentenone (15) in the same procedure as described above.

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Details 詳細情報について

  • CRID
    1390282681441650176
  • NII Article ID
    130000028842
  • DOI
    10.1271/bbb1961.45.295
  • COI
    1:CAS:528:DyaL3MXks1WmtL8%3D
  • ISSN
    18811280
    00021369
  • Text Lang
    en
  • Data Source
    • JaLC
    • Crossref
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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