SULFUR AND THE ENEDIYNE ANTIBIOTICS

被引:4
作者
NICOLAOU, KC [1 ]
SMITH, AL [1 ]
机构
[1] UNIV CALIF SAN DIEGO, DEPT CHEM, LA JOLLA, CA 92093 USA
来源
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1993年 / 74卷 / 1-4期
基金
美国国家卫生研究院;
关键词
D O I
10.1080/10426509308038100
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Some of our studies in the area of the enediyne antibiotics are discussed, with particular emphasis on the involvement of sulfur in these compounds. First, a model study for the ABC-ring system of the calicheamicin gamma1I oligosaccharide involving a [3,3]-sigmatropic rearrangement is described which enabled the stereoselective installation of the 4-thio substituent on the B-ring and which served as the cornerstone for the first synthesis of the entire oligosaccharide fragment. The first enantioselective synthesis of (-)-calicheamicinone is then described. Finally, a novel triggering device for a dynemicin mimic based upon a 2-(phenylsulfonyl)ethyl carbamate is described which led to the synthesis of an extremely potent antitumor agent.
引用
收藏
页码:47 / 58
页数:12
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