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

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)897-901
Number of pages5
JournalNatural product communications
Volume8
Issue number7
Publication statusPublished - 2013 Aug 2

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Keywords

  • Cyclopentanedione
  • Enzymatic reduction
  • Formal synthesis
  • Madindoline

ASJC Scopus subject areas

  • Pharmacology
  • Plant Science
  • Drug Discovery
  • Complementary and alternative medicine

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