Asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C

被引:9
|
作者
Davies, Stephen G. [1 ]
Roberts, Paul M. [1 ]
Shah, Rushabh S. [1 ]
Thomson, James E. [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
关键词
Alkaloid; Conjugate addition; Nakinadine; SuperQuat; AMINO ACID MOIETY; NATURAL-PRODUCTS; DEBENZYLATION; ALCOHOLS;
D O I
10.1016/j.tetlet.2013.09.043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first asymmetric synthesis of the marine alkaloid (-)-(S)-nakinadine C is described. This synthesis employs the conjugate addition of lithium dibenzylamide to an N-alpha-phenylacryloyl SuperQuat derivative followed by diastereoselective protonation of the intermediate enolate using 2-pyridone as the key step to introduce the stereochemistry. (-)-(S)-Nakinadine C was isolated in 13% yield over 9 steps from commercially available atropic acid, 98:2 dr [(Z):(E) ratio] and >99% ee. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6423 / 6426
页数:4
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