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 |
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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 journal › Article
}
TY - JOUR
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
Y1 - 2013
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
UR - http://www.scopus.com/inward/record.url?scp=84880771722&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84880771722&partnerID=8YFLogxK
M3 - Article
C2 - 23980418
AN - SCOPUS:84880771722
VL - 8
SP - 897
EP - 901
JO - Natural Product Communications
JF - Natural Product Communications
SN - 1934-578X
IS - 7
ER -