Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals

被引：41

作者：

Du, W

Kaskar, B

Blumbergs, P

Subramanian, PK

Curran, DP ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

[2] Ash Stevens Inc, Detroit, MI 48202 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2003年 / 11卷 / 03期

关键词：

D O I：

10.1016/S0968-0896(02)00437-6

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：451 / 458

页数：8

共 40 条

[11] ABSOLUTE RATE CONSTANTS FOR THE ADDITION OF TRIETHYLSILYL RADICALS TO VARIOUS UNSATURATED-COMPOUNDS [J].