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Synlett 2009(18): 3040-3042  
DOI: 10.1055/s-0029-1218296
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Concise Total Synthesis of (±)-Crinine

Jian-Dong Liu, Shao-Hua Wang, Fu-Min Zhang, Yong-Qiang Tu*, Yong-Qiang Zhang
State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: tuyq@lzu.edu.cn;
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Publication History

Received 7 July 2009
Publication Date:
13 October 2009 (online)

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Abstract

The concise total synthesis of (±)-crinine was accomplished in 24% overall yield and eleven steps starting from an easily available allylic alcohol. The key step of the current synthesis involved the NBS-promoted semipinacol rearrangement reaction of allylic alcohols. The hydroindole skeleton with the sterically congested quaternary carbon center was established concisely by utilizing this semipinacol rearrangement followed by a combination of intramolecular aldol and aza-Michael reactions.

Key words

aldol reaction - alkaloids - aza-Michael reaction - semi­pinacol rearrangement - total synthesis