HIGHLY STEREOCONTROLLED AND EFFICIENT PREPARATION OF THE PROTECTED, ESTERIFICATION-READY DOCETAXEL (TAXOTERE) SIDE-CHAIN

Authors
KANAZAWA AM DENIS JN GREENE AE
Citation
Am. Kanazawa et al., HIGHLY STEREOCONTROLLED AND EFFICIENT PREPARATION OF THE PROTECTED, ESTERIFICATION-READY DOCETAXEL (TAXOTERE) SIDE-CHAIN, Journal of organic chemistry, 59(6), 1994, pp. 1238-1240
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
59
Issue
6
Year of publication
1994
Pages
1238 - 1240
Database
ISI
SICI code
0022-3263(1994)59:6<1238:HSAEPO>2.0.ZU;2-#
Abstract
A high-yield synthesis of the p-methoxybenzylidene-protected docetaxel (Taxotere) side chain, a useful derivative for efficient, epimerizati on-free esterification of the 7,10-bis[(trichloroethoxy)carbonyl] deri vative of 10-desacetylbaccatin III for the preparation of docetaxel, h as been effected; the C-4 and C-5 stereocenters of the 1,3-oxazolidine are generated with complete (greater-than-or-equal-to 99%) stereocont rol whereas that at C-2 is produced with 96% selectivity.