A concise and stereoselective synthesis of the A-ring fragment of the gambieric acids

被引:61
作者
Clark, JS [1 ]
Fessard, TC [1 ]
Wilson, C [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
关键词
D O I
10.1021/ol049483s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The A-ring fragment of the gambieric acids has been prepared by a short and efficient route. The key 3(2H)-furanone intermediate has been obtained by [2,3] rearrangement of an allylic oxonium ylide generated from intramolecular reaction of a crotyl ether with a copper carbenoid. A single stereogenic center has been set by using a chiral pool starting material and the other three have been established by using highly diastereoselective substrate-controlled transformations.
引用
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页码:1773 / 1776
页数:4
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