摘要
在一些抗病毒药物或其前体的结构中包含有γ－内酯结构片段，因此它的合成具有十分重要的前景．由于内酯环的立体构型与药物的生物活性之间有着密切的相关性而显得更为重要．虽然有关γ－内酯的合成已有不少报道，但高立体选择性的合成方法至今尚不多见．本文报道了一种高...
A simple approach to highly stereoselective synthesis of trans β methoxycarbonyl γ aryl γ butyrolactones(5a 5c) is reported. Methoxycarbonylmethyltriphenylarsonium bromide(1) in dimethyl ethylene glycol was reacted with 2,2 dimethyl 1,3 dioxa 5 p methoxybenzal 4,6 dione(2a) in the presence of K 2CO 3 and trace of water at room temperature, to give trans β methoxycarbonyl γ p methoxyphenyl γ butyrolactone(5a) with 64% yield, whereas 1,2 cis cyclopropane derivatives(3b and 3c) were isolated when started from 2b or 2c, under same conditions. The γ butyrolactones 5b or 5c were obtained with 62% and 57% yields when compounds 3b or 3c was further heated in acetone water. The structures of 5a 5c were established on the basis of IR, 1H and 13 C NMR, MS and elemental analyses, and their configurations were assigned via 2D proton NOESY spectrum of compound 5c.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
1998年第10期1614-1616,共3页
Chemical Journal of Chinese Universities
基金
中国科学院上海金属有机化学开放实验室
国家自然科学基金
