D-homoannulation of 17α,21-dihydroxy-20-keto steroids (corticosteroids)
- 作者：Angelo Liguori ; Francesca Perri ; Carlo Siciliano
- 关键词：D-homosteroids ; 17 ; 21-Dihydroxy-20-keto steroids ; Corticosteroids ; Rearrangement ; Aluminium trichloride ; Cyclic sulfites
- 刊名：Steroids
- 出版年：2006
- 期刊代码：142_0039128x
- 类别：bio
- 出版时间：December 2006
- 卷：71
- 期：13-14
- 页码：1091-1096
- 文件大小：420 K
摘要
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.