Synthesis of (+)-methyl phaseate and its isomer from (-)-.BETA.-pinene.

DOI DOI オープンアクセス
  • TAKAHASHI Shunya
    Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University
  • ORITANI Takayuki
    Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University
  • YAMASHITA Kyohei
    Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University

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説明

The total synthesis of (+)-methyl phaseate (2b) and its epimer (25) is described. The known β-ketoester (8), which was prepared from (-)-β-pinene (4), was converted to a key intermediate (5) via a 1, 4-dioxoester (7). The reaction of 5 with a lithium reagent of the acetylene TBDMS ether (6) in THF-HMPA at -70°C afforded the desired acetylene alcohol (17) and its epimer (18) in high yields. 17 was transformed into (+)-methyl phaseate (2b). From this synthetic work, the absolute configuration of natural (-)-phaseic acid (2a) was confirmed.

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詳細情報 詳細情報について

  • CRID
    1390001206468165504
  • NII論文ID
    110006324046
  • NII書誌ID
    AA00515312
  • DOI
    10.1271/bbb1961.53.2711
    10.1080/00021369.1989.10869704
  • COI
    1:CAS:528:DyaK3cXktVKlsLw%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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