The first total synthesis of discorhabdin A

被引:85
作者
Tohma, H [1 ]
Harayama, Y [1 ]
Hashizume, M [1 ]
Iwata, M [1 ]
Kiyono, Y [1 ]
Egi, M [1 ]
Kita, Y [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan
关键词
D O I
10.1021/ja0365330
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first stereoselective total synthesis of a potent antitumor alkaloid, discorhabdin A (1), which is a unique sulfur-containing pyrroloiminoquinone alkaloid, is described. The key step in the stereocontrolled total synthesis of 1 involves both a diastereoselective oxidative spirocyclization using a hypervalent iodine(III) reagent and an efficient construction of the labile and highly strained N,S-acetal skeleton. These methodologies provide a breakthrough in the total syntheses of these promising new antitumor agents, discorhabdins and their analogues, which should serve as valuable probes for structure-activity studies.
引用
收藏
页码:11235 / 11240
页数:6
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