高等学校化学学报

高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (5): 874.

• 研究简报 • 上一篇    下一篇

MK-287的对映选择性合成

史鸿鑫1, 林辉2, R. Bloch3, G. Mandville3   

  1. 1. 浙江工业大学, 浙江省绿色化学合成技术重点实验室, 杭州 310014;
    2. 浙江大学理学院化学系, 杭州310012;
    3. Université Paris-Sud, ICMO, 91405 Orsay Cédex, France
  • 收稿日期:2003-05-16 出版日期:2004-05-24 发布日期:2004-05-24
  • 通讯作者: 史鸿鑫(1955年出生),男,博士,教授,从事精细化学品合成与有机催化研究.E-mail:shihxin@zjut.edu.cn E-mail:shihxin@zjut.edu.cn
  • 基金资助:

    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

Enantioselective Synthesis of MK-287

SHI Hong-Xin1, LIN Hui2, R. Bloch3, G. Mandville3   

  1. 1. Zhejiang Key Lab of Green-chemical Synthetic Technology, Zhejiang University of Technology, Hangzhou 310014, China;
    2. Department of Chemistry, Institute of Science, Zhejiang University, Hangzhou 310012, China;
    3. Université de Paris-Sud, ICMO, 91405, Orsay Cédex, France
  • Received:2003-05-16 Online:2004-05-24 Published:2004-05-24

PDF (PC)

关键词: 对映选择性, 手性, MK-287

Abstract: (2″S,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-[5.2.1.02,6]-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.

Key words: Enantioselectivity, Chirality, MK-287

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