Total synthesis of (-)-nakadomarin A: alkyne ring-closing metathesis

被引：50

作者：

Jakubec, Pavol ^{[1
]}

Kyle, Andrew F. ^{[1
]}

Calleja, Jonas ^{[1
]}

Dixon, Darren J. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 46期

基金：

英国工程与自然科学研究理事会;

关键词：

Nakadomarin A; Total synthesis; Organocatalysis; Stereoselective synthesis; Michael addition; Nitro-Mannich reaction; Iminium ion; Alkyne ring-closing metathesis; Cascade; ENANTIOSELECTIVE CONJUGATE ADDITION; ASYMMETRIC TOTAL-SYNTHESIS; BETA-KETO PHOSPHONATES; METAL-CARBON BONDS; NAKADOMARIN-A; STEREOSELECTIVE-SYNTHESIS; TETRACYCLIC CORE; BIFUNCTIONAL ORGANOCATALYSTS; HOMOGENEOUS METATHESIS; ACETYLENE METATHESIS;

D O I：

10.1016/j.tetlet.2011.09.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 13-step, highly stereoselective synthesis of (-)-nakadomarin A has been achieved using the combination of a bifunctional organocatalyst controlled Michael addition, a nitro-Mannich/lactamization cascade, an alkyne ring-closing metathesis/syn-reduction, and furan/iminium ion cyclization/reduction as key steps. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6094 / 6097

页数：4

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