Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (06): 1291-1297.DOI: 10.6023/cjoc201304019 Previous Articles     Next Articles



冯涛a, 司长梅a, 刘如成a, 范翔b, 魏邦国a   

  1. a 复旦大学化学系 上海 200043;
    b 华东理工大学生物工程学院 上海 200237
  • 收稿日期:2013-04-15 修回日期:2013-05-03 发布日期:2013-05-06
  • 通讯作者: 魏邦国
  • 基金资助:

    国家自然科学基金(Nos.21272041, 21072034)资助项目.

Asymmetric Allylation of N,O-Acetal and Application in the Synthesis of Epiquinamide and (+)-Febrifugine

Feng Taoa, Si Changmeia, Liu Ruchenga, Fan Xiangb, Wei Bangguoa   

  1. a Department of Chemistry, Fudan University, Shanghai 200043;
    b School of Biotechnology, East China University of Science and Technology, Shanghai 200237
  • Received:2013-04-15 Revised:2013-05-03 Published:2013-05-06
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos.21272041, 21072034).

Lewis acid catalyzed asymmetric allylation of N,O-acetal 7 with allyltrimethylsilane was developed for the synthesis of compounds 9, 10 and 16 with high disasterselectivities.A key middle compound 21 for synthesis of (-)-epiquinamide (1) was easily prepared from allylation product 16.In continuation of our work, a convenient method for synthesis of (+)-febrifugine (3) was also described from the mixture of (2S,3S) and (2S,3R)-9.Therefore, a possible approach for gram scale preparation of (+)-febrifugine (3) from glutamic acid was achieved.

Key words: N,O-acetal, allylation, glutamic acid, Epiquinamide, (+)-Febrifugine