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

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interleukin-6
Interleukin-6
Carbon
synthesis
carbon
madindoline A
cyclopentenone

Keywords

  • Cyclopentanedione
  • Enzymatic reduction
  • Formal synthesis
  • Madindoline

ASJC Scopus subject areas

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

Cite this

Formal synthesis of (+)-madindoline A, a potent IL-6 inhibitor, utilizing enzymatic discrimination of quaternary carbon. / Shimizu, Ken Ichi; Tomita, Mina; Fuhshuku, Ken Ichi; Sugai, Takeshi; Shoji, Mitsuru.

In: Natural Product Communications, Vol. 8, No. 7, 2013, p. 897-901.

Research output: Contribution to journalArticle

Shimizu, Ken Ichi ; Tomita, Mina ; Fuhshuku, Ken Ichi ; Sugai, Takeshi ; Shoji, Mitsuru. / Formal synthesis of (+)-madindoline A, a potent IL-6 inhibitor, utilizing enzymatic discrimination of quaternary carbon. In: Natural Product Communications. 2013 ; Vol. 8, No. 7. pp. 897-901.
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AU - Sugai, Takeshi

AU - Shoji, Mitsuru

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