Exploring chemical diversity of epoxyquinoid natural products: Synthesis and biological activity of (-)-jesterone and related molecules

被引:78
作者
Hu, YB
Li, CM
Kulkarni, BA
Strobel, G
Lobkovsky, E
Torczynski, RM
Porco, JA
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Streamlined Synth, Metcalf Ctr Sci & Engn, Boston, MA 02215 USA
[3] Montana State Univ, Dept Plant Sci, Bozeman, MT 59717 USA
[4] Cornell Univ, Baker Lab, Dept Chem, Ithaca, NY 14853 USA
[5] Cytoclonal Pharmaceut Inc, Dallas, TX 75235 USA
关键词
D O I
10.1021/ol0159367
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Enantioselective syntheses of the potent antifungal agent (-)-jesterone, its hydroxy epimer, and a dimeric quinone epoxide derivative are reported. The synthesis involves diastereoselective epoxidation of a chiral quinone monoketal derivative and regio and stereoselective reduction of a quinone epoxide intermediate.
引用
收藏
页码:1649 / 1652
页数:4
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