Formal synthesis of (+)-madindoline A, a potent IL-6 inhibitor, utilizing enzymatic discrimination of quaternary carbon

Ken Ichi Shimizu, Mina Tomita, Ken Ichi Fuhshuku, Takeshi Sugai, Mitsuru Shoji

研究成果: Article査読

5 被引用数 (Scopus)

抄録

A formal synthesis of (+)-madindoline A was achieved. The Sunazuka's key intermediate, (4R,5S)-(-)-3-butyl-4-(tert-butyldimethylsiloxy)-5- methoxycarbonyl-2,5-dimethyl-2-cyclopentenone, was synthesized from easily available (2S,3S)-3-acetoxy-2-ethenyl-2-methylcyclopentanone. The starting material was reliably supplied by a chemo-enzymatic procedure in enantiomerically pure form. The synthesis was performed by straightforward transformations involving enone formation and regioselective introduction of the two alkyl side chains.

本文言語English
ページ(範囲)897-901
ページ数5
ジャーナルNatural product communications
8
7
DOI
出版ステータスPublished - 2013 7月

ASJC Scopus subject areas

  • 薬理学
  • 植物科学
  • 創薬
  • 補完代替医療

フィンガープリント

「Formal synthesis of (+)-madindoline A, a potent IL-6 inhibitor, utilizing enzymatic discrimination of quaternary carbon」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル