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

doi:10.6023/cjoc201304019

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

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3-羟基哌啶N,O-缩醛的不对称烯丙基化反应及在Epiquinamide和(+)-Febrifugine合成中的应用

冯涛^a, 司长梅^a, 刘如成^a, 范翔^b, 魏邦国^a

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 E-mail:bgwei1974@fudan.edu.cn
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 Tao^a, Si Changmei^a, Liu Rucheng^a, Fan Xiang^b, Wei Bangguo^a

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

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Feng Tao, Si Changmei, Liu Rucheng, Fan Xiang, Wei Bangguo. Asymmetric Allylation of N,O-Acetal and Application in the Synthesis of Epiquinamide and (+)-Febrifugine[J]. Chin. J. Org. Chem., 2013, 33(06): 1291-1297.

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3-羟基哌啶N,O-缩醛的不对称烯丙基化反应及在Epiquinamide和(+)-Febrifugine合成中的应用

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

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