Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3237-3243.DOI: 10.6023/cjoc201904074 Previous Articles     Next Articles

通过Michael加成引发分子间的环丙烷化反应高效合成螺环嘧啶核苷

郝二军a, 张庆a, 张齐英a*(), 渠桂荣a, 杨西宁b, 郭海明a*()   

  1. a河南师范大学化学化工学院 精细化学品绿色制造河南省协同创新中心 河南省有机功能分子与药物创新重点实验室 河南新乡 453007
    b 新乡拓新药业股份有限公司 河南新乡 453000
  • 收稿日期:2019-04-30 出版日期:2019-11-25 发布日期:2019-06-24
  • 通讯作者: 张齐英,郭海明 E-mail:zhangqiying@htu.edu.cn;ghm@htu.edu.cn
  • 基金资助:
    国家自然科学基金(21602045);国家自然科学基金(U1604283);河南省博士后科学基金(2015071);高等学校学科创新引智计划(111计划);高等学校学科创新引智计划(D17007)

Efficient Synthesis of Spirocyclic Nucleosides via Michael Addition-Initiated Intermolecular Cyclopropanation Reaction

Hao Erjuna, Zhang Qinga, Zhang Qiyinga*(), Qu Guironga, Yang Xiningb, Guo Haiminga*()   

  1. aHenan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
    b Xinxiang Tuoxin Pharmaceutical Co., Ltd., Xinxiang, Henan 453000
  • Received:2019-04-30 Online:2019-11-25 Published:2019-06-24
  • Contact: Zhang Qiying,Guo Haiming E-mail:zhangqiying@htu.edu.cn;ghm@htu.edu.cn
  • Supported by:
    the National Natural Science Foundation of China(21602045);the National Natural Science Foundation of China(U1604283);the Henan Postdoctoral Science Foundation Funded Project(2015071);Overseas Expertise Introduction Project for Discipline Innovation(111计划);Overseas Expertise Introduction Project for Discipline Innovation(D17007)

An efficient route to synthesize 2'-spiro[2-oxocyclopentyl]cyclopropyl nucleoside analogues via KOtBu promoted Michael addition-initiated cyclopropanation reactions of α-thymine acrylates with α-chloro-cycloalkanones has been developed. A wide range of C(2')-spirocyclic modified nucleoside analogues were obtained with excellent diastereoselectivities (>20:1) and good yields (up to 85%).