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Synthesis 2011(22): 3675-3679  
DOI: 10.1055/s-0030-1260243
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Cascade Sequence to Indoloquinolizidines and Its Application in the Synthesis of epi-Geissochizol

Xiaoyu Wu*a, Yao Zhangb, Xiaoyang Daia, Huihui Fanga, Jie Chena, Weiguo Cao*a, Gang Zhao*b
a Department of Chemistry, Shanghai University, 99 Shangda Rd, Shanghai 200444, P. R. of China
Fax: +86(21)66134594; e-Mail: wuxy@shu.edu.cn; e-Mail: wgcao@staff.shu.edu.cn;
b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
e-Mail: zhaog@mail.sioc.ac.cn;
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Publication History

Received 18 July 2011
Publication Date:
27 September 2011 (online)

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Abstract

An organocatalyzed one-pot Michael addition and Pictet­-Spengler sequence utilizing β-keto amide and aliphatic α,β-unsaturated aldehydes was developed, which provided access to highly substituted indolo[2,3-a]quinolizidines as a mixture of keto and enol tautomers. Such tautomeric pairs were transformed into stable compounds with an E-ethylidenyl group in telescoped steps. This method was successfully applied in the synthesis of epi-geisso­schizol.

Key words

Michael addition - organocatalysis - cyclization - enan­tio­selectivity - reduction

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