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 Jul |
Keywords
- Cyclopentanedione
- Enzymatic reduction
- Formal synthesis
- Madindoline
ASJC Scopus subject areas
- Pharmacology
- Plant Science
- Drug Discovery
- Complementary and alternative medicine