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Synthesis 2011(21): 3439-3446  
DOI: 10.1055/s-0030-1260194
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Multicomponent Reaction between α-Substituted Acroleins, Nitroalkanes and Paraformaldehyde: Efficient Construction of Nitro δ-Lactol

Guoxi Xionga,b, Mohui Weia, Yirong Zhoua, Yungui Lia, Fanglin Zhang*a, Yuefa Gong*a
a Department of Chemistry, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, P. R. of China
Fax: +86(27)87543632; e-Mail: hyvzfl@gmail.com; e-Mail: gongyf@mail.hust.edu.cn;
b Research and Development Center, China Tobacco Hubei Industrial Co. Ltd., Wuhan 430040, P. R. of China
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Publication History

Received 5 July 2011
Publication Date:
01 September 2011 (online)

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Abstract

A base-catalyzed multicomponent cascade reaction between α-substituted acroleins, nitroalkanes, and paraformaldehyde that proceeded smoothly to give high yields of functionalized δ-lactols under mild conditions, is described. This methodology is useful in the development of a concise synthetic route to natural products (±)-manzacidin A and C.

Key words

multicomponent reaction - α-substituted acroleins - 1,8-diazabicyclo[5.4.0]undec-7-ene - δ-lactols

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