Bengazoles C-G from the sponge Jaspis sp synthesis of the side chain and determination of absolute configuration

被引:45
作者
Searle, PA [1 ]
Richter, RK [1 ]
Molinski, TF [1 ]
机构
[1] UNIV CALIF DAVIS,DEPT CHEM,DAVIS,CA 95616
关键词
D O I
10.1021/jo952261a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Five new antifungal bengazoles (C-G) were isolated and fully characterized from a marine sponge of the genus Jaspis sp. Bengazoles- C-G, together with the known bengazoles A and B, comprise a bomologous series of n, iso, and anteiso fatty acid esters (C-13-C-16) Of the same heterocyclic bis-(oxazolyl)methanol parent. The complete relative and absolute configurations of the bengazoles were determined by application of the modified Mosher method and interpretation of exciton coupling in the CD spectra of the tetra-p-bromobenzoate derivatives of bengazole A and that of a model tetrol synthesized in seven steps from L-fucose.
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收藏
页码:4073 / 4079
页数:7
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