Semisynthesis of D-ring modified taxoids: Novel thia derivatives of docetaxel

Authors
Merckle, L Dubois, J Place, E Thoret, S Gueritte, F Guenard, D Poupat, C Ahond, A Potier, P
Citation
L. Merckle et al., Semisynthesis of D-ring modified taxoids: Novel thia derivatives of docetaxel, J ORG CHEM, 66(15), 2001, pp. 5058-5065
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
15
Year of publication
2001
Pages
5058 - 5065
Database
ISI
SICI code
0022-3263(20010727)66:15<5058:SODMTN>2.0.ZU;2-Q
Abstract
Two novel 5(20)-thia analogues of docetaxel have been synthesized from 10-d eacetylbaccatin III or taxine B and isotaxine B. The key step of these synt heses is the concomitant thietane ring formation and acetylation of the ter tiary alcohol at C-4. Both compounds are less cytotoxic than docetaxel but have divergent activity on microtubule disassembly.