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

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 48期

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

页码：6423 / 6426

页数：4

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