Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal V

被引:23
作者
Lazarski, Kiel E. [1 ]
Akpinar, Berkcan [1 ]
Thomson, Regan J. [1 ]
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词
Maoecrystal V; Etherification; Oxy-1,4-addition; INTRAMOLECULAR HYDROGEN ABSTRACTION; GENERATION; FUNCTIONALIZATION; HYDROXYLATION; EFFICIENT;
D O I
10.1016/j.tetlet.2012.11.135
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C-H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C-O bond but resulted in the undesired stereochemistry. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:635 / 637
页数:3
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