MK-287的对映选择性合成  

Enantioselective Synthesis of MK-287

作　　者：史鸿鑫[1] 林辉[2] R.Bloch G.Mandville 

机构地区：[1]浙江工业大学 [2]浙江大学理学院化学系,杭州310012 [3]Université de Paris-Sud

出　　处：《高等学校化学学报》2004年第5期874-876,共3页Chemical Journal of Chinese Universities

基　　金：中法政府科技合作课题 (批准号 :1996-4 );浙江省科技厅基金资助

摘　　要：錝,5″S)-2-{3′-Methoxy-2′-propoxy-5′-[5″-(3,4,5-trimethoxyphenyl)tetrahydrofuran-2″-yl] phenylsulfonyl}ethanol(MK-287) which was potent PAF antagonist, was enantioselectively synthesized in eight steps by addition, oxidation, hot decomposition, hydrogenation and so on from (-)-4,10-dioxatricyclo-[5.2.1.0 2,6]-decene-3-ole(1). Asymmetry was introduced using the nucleophilic addition of the triisopropoxytitanium to the lactol 1. The second asymmetric center was installed by a highly stereocontrolled acid-assisted reduction with sodium cyanoborohydride of the hemiketal formed. The product MK-287 was optically pure.錝,5″S)-2-{3′-Methoxy-2′-propoxy-5′-[5″-(3,4,5-trimethoxyphenyl)tetrahydrofuran-2″-yl] phenylsulfonyl}ethanol(MK-287) which was potent PAF antagonist, was enantioselectively synthesized in eight steps by addition, oxidation, hot decomposition, hydrogenation and so on from (-)-4,10-dioxatricyclo-[5.2.1.0 2,6]-decene-3-ole(1). Asymmetry was introduced using the nucleophilic addition of the triisopropoxytitanium to the lactol 1. The second asymmetric center was installed by a highly stereocontrolled acid-assisted reduction with sodium cyanoborohydride of the hemiketal formed. The product MK-287 was optically pure.

关 键 词：MK-287 对映选择性合成 反式-2 5-二取代四氢呋喃 血小板活化因子 拮抗剂 

分 类 号：R914.5[医药卫生—药物化学]