Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals
Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals
复制标题
DOI：
10.1016/s0968-0896(02)00437-6
复制
发表时间：
2003-02-06
影响因子：
3.5
通讯作者：
Curran, DP
中科院分区：
文献类型：
--
作者：
Du, W;Kaskar, B;Curran, DP
报道了巯基或酸促进的甲硅烷基与喜树碱的加成反应。在105 ℃下，形成7-甲硅烷基喜树碱（优选的）和12-甲硅烷基喜树碱的混合物，同时形成大量回收的喜树碱。在160 ℃时，优先形成12-甲硅烷基异构体，但总质量平衡显著降低。在从喜树碱和10-羟基喜树碱的DB-67（7-叔丁基二甲基甲硅烷基-10-羟基喜树碱）的短半合成中，具有硅烷基自由基加成的特征。(C)2002爱思唯尔科技有限公司版权所有。
Thiol- or acid-promoted additions of silyl radicals to camptothecin are reported. At 105 degreesC, mixtures of 7-silyl (favored) and 12-silyl camptothecins are formed alongside substantial amounts of recovered camptothecin. At 160degreesC, 12-silyl isomers are formed preferentially, but the total mass balance is substantially reduced. The silyl radical addition is featured in short semisyntheses of DB-67 (7-tert-butyldimethylsilyl-10-hydroxy camptothecin) from both camptothecin and 10-hydroxycamptothecin. (C) 2002 Elsevier Science Ltd. All rights reserved.