SUPPRESSION OF THE MATTOX REARRANGEMENT OF 16-ALPHA-CYANOPREDNISOLONES IN ACID - SYNTHESIS OF METHYL 16-ALPHA-PREDNISOLONECARBOXYLATES

Authors
YOU ZQ KHALIL MA KO DH LEE HJ
Citation
Zq. You et al., SUPPRESSION OF THE MATTOX REARRANGEMENT OF 16-ALPHA-CYANOPREDNISOLONES IN ACID - SYNTHESIS OF METHYL 16-ALPHA-PREDNISOLONECARBOXYLATES, Tetrahedron letters, 36(19), 1995, pp. 3303-3306
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
19
Year of publication
1995
Pages
3303 - 3306
Database
ISI
SICI code
0040-4039(1995)36:19<3303:SOTMRO>2.0.ZU;2-W
Abstract
Prednisolone derivatives with a 16 alpha-methyl carboxylate group were synthesized by a novel procedure of 1,3-dipole addition of fulminic a cid to 21-acetyloxy-11 beta-hydroxy-3,20-dioxo-1,4,16-pregnatriene, fo llowed by base-catalyzed ring opening of the resulting isoxazoline to yield a 16 alpha-cyanoprednisolone derivative and treatment of the nit rile with methanolic HCl. Conversion of the cyanosteroids in the acid to the corresponding methyl carboxylates was achieved with or without the Matron rearrangement by controlling reaction temperature and prote ctive group for the 21-OH.