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

doi:10.1177/1934578x1300800710

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 › peer-review

5 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
DOIs	https://doi.org/10.1177/1934578x1300800710
Publication status	Published - 2013 Jul

Keywords

Cyclopentanedione
Enzymatic reduction
Formal synthesis
Madindoline

ASJC Scopus subject areas

Pharmacology
Plant Science
Drug Discovery
Complementary and alternative medicine

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

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.",

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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 - 2013/7

Y1 - 2013/7

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.

KW - Cyclopentanedione

KW - Enzymatic reduction

KW - Formal synthesis

KW - Madindoline

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