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.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
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
