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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Item Type: |
Article
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Du, W | | | | Kaskar, B | | | | Blumbergs, P | | | | Subramanian, PK | | | | Curran, DP | curran@pitt.edu | CURRAN | |
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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-dev.library.pitt.edu/id/eprint/20479 |
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