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

Du, W and Kaskar, B and Blumbergs, P and Subramanian, PK and Curran, DP (2003) Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals. Bioorganic and Medicinal Chemistry, 11 (3). 451 - 458. ISSN 0968-0896

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Abstract

Thiol- or acid-promoted additions of silyl radicals to camptothecin are reported. At 105°C, mixtures of 7-silyl (favored) and 12-silyl camptothecins are formed alongside substantial amounts of recovered camptothecin. At 160°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. © 2002 Elsevier Science Ltd. All rights reserved.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Du, W
Kaskar, B
Blumbergs, P
Subramanian, PK
Curran, DPcurran@pitt.eduCURRAN
Date: 1 February 2003
Date Type: Publication
Journal or Publication Title: Bioorganic and Medicinal Chemistry
Volume: 11
Number: 3
Page Range: 451 - 458
DOI or Unique Handle: 10.1016/s0968-0896(02)00437-6
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0968-0896
MeSH Headings: Camptothecin--analogs & derivatives; Camptothecin--chemical synthesis; Camptothecin--chemistry; Free Radicals--chemistry; Hot Temperature; Isomerism; Organosilicon Compounds--chemical synthesis; Organosilicon Compounds--chemistry; Sulfhydryl Compounds--chemical synthesis; Sulfhydryl Compounds--chemistry
PubMed ID: 12517440
Date Deposited: 07 Feb 2014 00:03
Last Modified: 29 Jan 2019 15:55
URI: http://d-scholarship.pitt.edu/id/eprint/20479

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