D-homoannulation of 17alpha,21-dihydroxy-20-keto steroids (corticosteroids).
Synthetic corticosteroids are widely used as anti-inflammatory agents. Mechanisms of their degradation continue to be studied. D-ring homoannulation is a well-known metabolic pathway for steroids in vivo. The rearrangement with aluminium trichloride of the commercial anti-inflammatory drugs hydrocortisone, cortisone and dexamethasone is here presented. The structures of the corresponding 17a-keto-17-hydroxy-D-homosteroids are established by mono- and two-dimensional NMR analysis. Inversion of the alpha-configuration of C-16 is observed in the Lewis acid assisted D-homoannulation of dexamethasone.
Liguori
Angelo
A
Dipartimento di Scienze Farmaceutiche, Università degli Studi della Calabria, Via P. Bucci cubo 15/c, I-87036 Arcavacata di Rende, CS, Italy. A.Liguori@unical.it
Perri
Francesca
F
Siciliano
Carlo
C
D000305:Adrenal Cortex Hormones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000305:Adrenal Cortex Hormones