Geometry-selective synthesis of the unsaturated side chains of the isodomoic acids

被引:3
作者
Fleary-Roberts, Nadia [1 ]
Lemiere, Gilles [1 ]
Clayden, Jonathan [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
基金
英国工程与自然科学研究理事会;
关键词
Alkene; Coupling; Metalcatalysed; Natural product synthesis; ORGANIC-SYNTHESIS; CONVERSION; REAGENT;
D O I
10.1016/j.tet.2015.02.055
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three unsaturated vinylic or allylic halides were made in enantiomerically pure form, ready for coupling with a vinyl metal as part of a divergent strategy for the synthesis of members of the domoic/isodomoic acid family and their analogues. The trisubstituted alkene 3 was made by an E-selective Wittig reaction, while 4 and 5 were made by stereoselective hydrometallation or hydroboration of an alkyne. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7204 / 7208
页数:5
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