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

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	897-901
Number of pages	5
Journal	Natural product communications
Volume	8
Issue number	7
Publication status	Published - 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

Cite this

Shimizu, K. I., Tomita, M., Fuhshuku, K. I., Sugai, T., & Shoji, M. (2013). Formal synthesis of (+)-madindoline A, a potent IL-6 inhibitor, utilizing enzymatic discrimination of quaternary carbon. Natural product communications, 8(7), 897-901.

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T1 - Formal synthesis of (+)-madindoline A, a potent IL-6 inhibitor, utilizing enzymatic discrimination of quaternary carbon

AU - Shimizu, Ken Ichi

AU - Tomita, Mina

AU - Fuhshuku, Ken Ichi

AU - Sugai, Takeshi

AU - Shoji, Mitsuru

PY - 2013/8/2

Y1 - 2013/8/2

N2 - 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.

AB - 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.

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KW - Enzymatic reduction

KW - Formal synthesis

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

Abstract

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Keywords

ASJC Scopus subject areas

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