Saeed Aamer
Department of Chemistry, Quaid-i-Azam University, Islamabad-45320, Pakistan.
Z Naturforsch C J Biosci. 2003 Sep-Oct;58(9-10):691-6. doi: 10.1515/znc-2003-9-1017.
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.
已实现从球形蒙氏木中分离得到的蒙氏香豆素[（3S）-6,8-二羟基-3-苯基-3,4-二氢异香豆素]的简单立体选择性合成。苯甲酰氯与3,5-二甲氧基高邻苯二甲酸缩合得到6,8-二甲氧基-3-苯基异香豆素（3），其经顺序皂化和酯化得到酮酯5。用面包酵母对后者进行对映选择性还原，直接以良好的对映选择性得到（3S）-6,8-二甲氧基-3-苯基-3,4-二氢异香豆素（6），其脱甲基后得到蒙氏香豆素。对所有合成化合物进行了体外抗真菌活性检测。
