| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 2029045 | Steroids | 2006 | 6 Pages |
Abstract
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 α-configuration of C-16 is observed in the Lewis acid assisted D-homoannulation of dexamethasone.
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Authors
Angelo Liguori, Francesca Perri, Carlo Siciliano,