SYNTHESIS OF A PACLITAXEL ISOMER - C-2-ACETOXY-C-4-BENZOATE PACLITAXEL

Authors
CHEN SH FARINA V VYAS DM DOYLE TW
Citation
Sh. Chen et al., SYNTHESIS OF A PACLITAXEL ISOMER - C-2-ACETOXY-C-4-BENZOATE PACLITAXEL, Bioorganic & medicinal chemistry letters, 8(16), 1998, pp. 2227-2230
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
8
Issue
16
Year of publication
1998
Pages
2227 - 2230
Database
ISI
SICI code
0960-894X(1998)8:16<2227:SOAPI->2.0.ZU;2-C
Abstract
A synthesis of the C-2-acetoxy-C-4-benzoate paclitaxel 2 is described. This analog has the substituents at C-2 and C-4 transposed. The key s teps in the synthesis include the sequential use of Red-Al as reducing agent for the regioselective reduction of the C-2 benzoate and the C- 4 acetoxy within the baccatin core. Iso-paclitaxel 2 was considerably less potent than paclitaxel in tubulin polymerization and in vitro cyt otoxicity assays. (C) 1998 Elsevier Science Ltd. All rights reserved.