Synthesis of the antifungal macrolide antibiotic (+)-roxaticin

被引:85
作者
Evans, DA [1 ]
Connell, BT [1 ]
机构
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ja027638q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The total synthesis of the antifungal macrolide antibiotic roxaticin has been accomplished. The synthesis relies principally on aldol and directed reduction steps to construct the extended 1,3-polyol array present in the natural product. Three principal nonpolyene containing fragments were assembled and then coupled using Julia olefination and methyl ketone aldol addition reactions. A series of functionalization reactions incorporated the sensitive polyene and provided the protected roxaticin seco-acid, which was lactonized in good yield. Acidic deprotection completed this convergent synthesis of roxaticin.
引用
收藏
页码:10899 / 10905
页数:7
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