Stereochemical elucidation of the pentacyclopropane antifungal agent FR-900848

被引:42
作者
Barrett, AGM [1 ]
Doubleday, WW [1 ]
Kasdorf, K [1 ]
Tustin, GJ [1 ]
机构
[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523
关键词
D O I
10.1021/jo960054k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Full structural elucidation of FR-900848, an antifungal pentacyclopropane nucleoside natural product from Streptoverticillium fervens, is reported. A series of model compounds were prepared using multiple asymmetric Simmons-Smith cyclopropanation reactions. Comparisons of spectroscopic data of synthetic alkenes 9 and 10, quatercyclopropanes 11 and 12, and imidazolidines 13 and 14 with FR-900848 and its degradation products 2, 3, and 4 were consistent with the full structural assignment of the natural product as structure 7.
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页码:3280 / 3288
页数:9
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