Unusual hydroxy-gamma-sultone byproducts of steroid 21-methanesulfonylation. An efficient synthesis of mometasone 17-furoate (Sch 32088)

Authors
Draper, RW Hu, B McPhail, A Puar, MS Vater, EJ Weber, L
Citation
Rw. Draper et al., Unusual hydroxy-gamma-sultone byproducts of steroid 21-methanesulfonylation. An efficient synthesis of mometasone 17-furoate (Sch 32088), TETRAHEDRON, 55(11), 1999, pp. 3355-3364
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
11
Year of publication
1999
Pages
3355 - 3364
Database
ISI
SICI code
0040-4020(19990312)55:11<3355:UHBOS2>2.0.ZU;2-3
Abstract
An efficient two stage synthesis of the steroid anti-inflammatory agent mom etasone 17-furoate (Sch 32088) 4 from 17 alpha,21-dihydroxy-16 alpha-methyl -9 beta,11 beta-oxidopregna-1,4-diene-3,20-dione 6 is described and the str uctures of unusual delta-hydroxy-gamma-sultone byproducts of 4-dimethylamin opyridine catalyzed methanesulfonylation of 21-hydroxy-20-ketosteroids are deduced. (C) 1999 Elsevier Science Ltd. All rights reserved.