A synthetic approach to nomofungin/communesin B

A synthetic approach to nomofungin/communesin B
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DOI:
10.1021/ol034407v
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发表时间:
2003-09-04
期刊:
影响因子:
5.2
通讯作者:
Funk, RL
Funk, RL
中科院分区:
化学1区
文献类型:
--
作者:
Crawley, SL;Funk, RL

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[图表]吲哚与氮杂-邻-亚二甲苯中间体的高度立体选择性分子内环加成作用影响细胞毒性天然产物communesin B的大部分环系统的快速构建。涉及邻醌甲基化物中间体的类似环加成提供了加合物,其清楚地揭示了诺莫芬净的结构归属是错误的。
[GRAPHICS]A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an orthoquinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.