46 STEREOCONTROLLED TOTAL SYNTHESIS OF PICROTOXANE SESQUITERPENOIDS, (-)-PICROTOXININ AND (+)-CORIAMYRTIN

DOI

Bibliographic Information

Other Title
  • 46 ピクロトキサン型セスキテルペノイド,(-)-ピクロトキシニンおよび(+)-コリアミルチンの全合成

Abstract

Stereocontrolled total synthesis of toxic sesquiterpenoids of picrotoxane type, (-)-picrotoxinin (1) and (+)-coriamyrtin (2) is described. The double cyclization of a conjugated cyclohexenone 4 afforded the isotwistane compounds, 10a and 10b, which were converted into properly functionalzed cis-hydrindane derivative 17 via novel bridgehead hydroxylation of the bicyclo[3.2.1]octan-2-one moiety in the isotwistane intermediate 5. Optical resolution of 17 was made and the resulting (+)-17 was converted into a common and key intermediate (-)-6, from which (-)-picrotoxinin (1) and (+)-coriamyrtin (2) were synthesized.

Journal

Details 詳細情報について

  • CRID
    1390282681050808704
  • NII Article ID
    110006678403
  • DOI
    10.24496/tennenyuki.26.0_352
  • ISSN
    24331856
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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