Alternative Synthesis of Chrysanthemic Acid<i>via</i>Tetrahydrofuran Derivatives

DOI DOI オープンアクセス
  • HIRAI Hajime
    Department of Agricultural Chemistry, Faculty of Agriculture, The University of Tokyo Research Department, Pesticide Division, Sumitomo Chemical Co., Ltd.
  • UEDA Kenzo
    Department of Agricultural Chemistry, Faculty of Agriculture, The University of Tokyo Research Department, Pesticide Division, Sumitomo Chemical Co., Ltd.
  • MATSUI Masanao
    Department of Agricultural Chemistry, Faculty of Agriculture, The University of Tokyo

書誌事項

タイトル別名
  • Alternative synthesis of chrysanthemic acid via tetrahydrofuran derivatives.

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説明

The olefination reaction between 2, 2, 5, 5-tetramethyltetrahydrofuran-3-one (II) and diethyl ethoxycarbonylmethylphosphonate afforded an isomeric mixture of the normal α, β-unsaturated ester (IIIa) and the endocyclic β, γ-unsaturated ester (IVa). Catalytic hydrogenation and subsequent hydrolysis of the mixture gave 2, 2, 5, 5-tetramethyltetrahydrofuryl-3-acetic acid (Vc). (Vc) was treated with thionyl chloride in the presence of zinc chloride to give the dichloroester (VII), from which trans-chrysanthemic acid was obtained by a known method. Pyrocin (VI) was also obtained in good yield from the saturated acid (Vc) by heating with BF3-etherate. The probable mechanism of the Wadsworth-Emmons reaction and the formation of the endocyclic double bond is discussed.

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詳細情報 詳細情報について

  • CRID
    1390282681444226816
  • NII論文ID
    130003525131
  • DOI
    10.1271/bbb1961.40.153
    10.1080/00021369.1976.10861992
  • COI
    1:CAS:528:DyaE28XhtVGku7c%3D
  • ISSN
    18811280
    00021369
  • 本文言語コード
    en
  • データソース種別
    • JaLC
    • Crossref
    • CiNii Articles
    • OpenAIRE
  • 抄録ライセンスフラグ
    使用不可

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