TANDEM RADICAL TRIFLUOROMETHYLATION NUCLEOPHILIC CYCLIZATION OF A GLUCOSE-DERIVED KETENE DITHIOACETAL - SYNTHESIS OF 5-DEOXY-5-C-TRIFLUOROMETHYL-ALDURONO-6,3-LACTONES

Authors
FOULARD G BRIGAUD T PORTELLA C
Citation
G. Foulard et al., TANDEM RADICAL TRIFLUOROMETHYLATION NUCLEOPHILIC CYCLIZATION OF A GLUCOSE-DERIVED KETENE DITHIOACETAL - SYNTHESIS OF 5-DEOXY-5-C-TRIFLUOROMETHYL-ALDURONO-6,3-LACTONES, Journal of fluorine chemistry, 91(2), 1998, pp. 179-183
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Journal of fluorine chemistry → ACNP
ISSN journal
00221139
Volume
91
Issue
2
Year of publication
1998
Pages
179 - 183
Database
ISI
SICI code
0022-1139(1998)91:2<179:TRTNCO>2.0.ZU;2-S
Abstract
A diastereoisomeric mixture of 5-C-trifluoromethylated analogs of D-gl ucuronolactone and L-iduronolactone was synthesized in a five-step pro cedure from 1,2-O-isopropylidene-alpha-D-glucofuranose. The key step i nvolves a tandem radical trifluoromethylation-nucleophilic cyclization of a ketene dithioacetal derived from propylidene-alpha-D-xylo-pentod ialdo-1,4-furanose. (C) 1998 Elsevier Science S.A. All rights reserved .