Ｈｙｐｅｒｆｏｒｉｎの触媒的不斉全合成研究

• 清水 洋平

  東京大学薬学部

• 施 世良

  東京大学薬学部

• 臼田　 裕之

  東京大学薬学部

• 金井 求

  東京大学薬学部

• 柴崎 正勝

  東京大学薬学部

書誌事項

タイトル別名

• Synthetic study of hyperforin

抄録

Hyperforin was isolated from western herb, St. John's wort (Hypericum perforatum). Hyperforin exhibits various biologic activities including mild anti-depressant activity, anti-malarial activity, inhibitory activity of human histone deacetylase, and CYP3A4 induction activity. And this compound has characteristic structure; highly substituted bicyclo[3.3.1]nonanone core, 4 asymmetric carbon center.<BR> To synthesize attractive natural compound, hyperforin, our group developed the catalytic asymmetric Diels-Alder reaction. This key reaction gave substituted cyclohexene which has 2 contiguous asymmetric centers in high yield and selectivity (93% yield, 96% ee, exo: endo = >33: 1).<BR> From this key intermediate, we already synthesized bicyclo core via Claisen rearrangement, intramolecular aldol cyclization as key intermediate.<BR> And model study revealed that additional oxidation was possible using vinylogous Pummerer rearrangement.

収録刊行物

• 反応と合成の進歩シンポジウム 発表要旨概要

  反応と合成の進歩シンポジウム 発表要旨概要 35 (0), 83-83, 2009

  日本薬学会化学系薬学部会

キーワード

• Diels-Alder reaction
• natural product
• Claisen rearrangement
• intramolecular aldol reaction
• vinylogous Pummerer rearrangement

詳細情報

• CRID: 1390001205635407104
• NII論文ID: 130006997892
• DOI: 10.14895/hannou.35.0.83.0
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可