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.
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收藏
页码：6094 / 6097
页数：4
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