STUDIES TOWARDS THE SYNTHESIS OF 16-ALPHA-CARBOXYPREDNISOLONES - CHEMISTRY OF C16 C17 FUSED BROMOISOXAZOLINES/

Authors
BACHER E DEMNITZ FWJ HURNI T
Citation
E. Bacher et al., STUDIES TOWARDS THE SYNTHESIS OF 16-ALPHA-CARBOXYPREDNISOLONES - CHEMISTRY OF C16 C17 FUSED BROMOISOXAZOLINES/, Tetrahedron, 53(42), 1997, pp. 14317-14326
Citations number
44
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
42
Year of publication
1997
Pages
14317 - 14326
Database
ISI
SICI code
0040-4020(1997)53:42<14317:STTSO1>2.0.ZU;2-P
Abstract
Bromonitrile-N-oxide adds to the enone 9b/c completely regio-and stere oselectively to form the bromoisoxazoline 10b/c. The latter can be tra nsformed into the nitrile 11, previously hydrolyzed(14) to the target 16 alpha-carbomethoxyprednisolone 4a a potentially locally active anti inflammatory steroid. The methoxyisoxazoline 12, prepared from 10b has proved surprisingly resistant to reductive cleavage of the N-O bond. (C) 1997 Elsevier Science Ltd.