Synthesis of montroumarin.
A simple stereoselective synthesis of montroumarin [(3S)-6,8-dihydroxy-3-phenyl-3,4-dihydroisocoumarin] isolated from Montrouziera sphaeroidea has been achieved. Condensation of benzoyl chloride with 3,5-dimethoxyhomophthalic acid afforded 6,8-dimethoxy-3-phenylisocoumarin (3) which on sequential saponification and esterification yielded the keto ester 5. Enantioselective reduction of the latter with baker's yeast directly furnished the (3S)-6,8-dimethoxy-3-phenyl-3,4-dihydroisocoumarin (6) in good enantioselectivity which on demethylation provided montroumarin. All of the synthesized compounds were examined in vitro for antifungal activity.
Saeed
Aamer
A
Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan. aamersaeed@yahoo.com
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000935:Antifungal Agents; D003374:Coumarins; D007202:Indicators and Reagents; C412057:montroumarin