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Synlett 2011(2): 207-210  
DOI: 10.1055/s-0030-1259288
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Studies Towards Crinine-Type Amaryllidaceae Alkaloids: Synthesis of (±)-Oxocrinine and Formal Synthesis of (±)-Crinine

Lijuan Yanga, Xuequan Wangb, Zhiqiang Panb, Ming Zhoub, Wen Chena, Xiaodong Yang*b
a Key Laboratory of Ethnic Medicine Resource Chemistry (Yunnan University of Nationalities), State Ethnic Affairs Commission & Ministry of Education, Kunming, Yunnan 650031, P. R. of China
b Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, P. R. of China
Fax: +86(871)5035538; e-Mail: xdyang@ynu.edu.cn;
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Publication History

Received 14 September 2010
Publication Date:
23 December 2010 (online)

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Abstract

A flexible strategy leading to the synthesis of crinine-type Amaryllidaceae alkaloids, (±)-oxocrinine and (±)-crinine, has been developed. A notable feature in this synthetic route is the construction of tetrahydro-1H-benzo[c]azepine framework using an intramolecular Heck reaction and the formation of the sterically congested spiro cyclohexenone intermediate with a Robinson annulation.

Key words

Amaryllidaceae alkaloids - crinine - oxocrinine - total synthesis - quaternary carbon

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CCDC 766391 contains the supplementary crystallographic data for compound 6b. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.