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

Abstract:

:Thiol- or acid-promoted additions of silyl radicals to camptothecin are reported. At 105 degrees C, mixtures of 7-silyl (favored) and 12-silyl camptothecins are formed alongside substantial amounts of recovered camptothecin. At 160 degrees C, 12-silyl isomers are formed preferentially, but the total mass balance is substantially reduced. The silyl radical addition is featured in short semi-syntheses of DB-67 (7-tert-butyldimethylsilyl-10-hydroxy camptothecin) from both camptothecin and 10-hydroxycamptothecin.

journal_name

Bioorg Med Chem

authors

Du W,Kaskar B,Blumbergs P,Subramanian PK,Curran DP

doi

10.1016/s0968-0896(02)00437-6

subject

Has Abstract

pub_date

2003-02-06 00:00:00

pages

451-8

issue

3

eissn

0968-0896

issn

1464-3391

pii

S0968089602004376

journal_volume

11

pub_type

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