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 | |
| Publication status | Published - 2013 |
Keywords
- Cyclopentanedione
- Enzymatic reduction
- Formal synthesis
- Madindoline
ASJC Scopus subject areas
- Pharmacology
- Plant Science
- Drug Discovery
- Complementary and alternative medicine
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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. https://doi.org/10.1177/1934578x1300800710