Synthesis of (-)-<i>ent</i>-Altholactone, (+)-7a-<i>epi</i>-Altholactone, (-)-<i>ent</i>-Isoaltholactone and (-)-7a-<i>epi</i>-Isoaltholactone from 2, 3-<i>O</i>-Cyclohexylidene-D-glyceraldehyde

  • HIRATATE Akira
    Department of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University
  • KIYOTA Hiromasa
    Department of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University
  • ORITANI Takayuki
    Department of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University

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  • 2,3-<i>O</i>-シクロヘキシリデン-D-グリセルアルデヒドから (-)-<i>ent</i>-アルトラクトン, (+)-7a-<i>epi</i>-アルトラクトン, (-)-<i>ent</i>-イソアルトラクトンおよび (-)-7a-<i>epi</i>-イソアルトラクトンの合成
  • Synthesis of (-)-ent-Altholactone, (+)-7a-epi-Altholactone, (-)-ent-Isoaltholactone and (-)-7a-epi-Isoaltholactone from 2,3-O-Cyclohexylidene-D-glyceraldehyde

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Abstract

Synthesis of the diastereomers of (+)-altholactone, an antitumor acetogenin from various Goniothalamus species, was achieved. Four isomers including 3a, 7a-trans-fused analogs were synthesized from 2, 3-O-cyclohexylidene-D-glyceraldehyde via twice separation of diastereomers.

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