Steroids—CXXI synthesis of halogenated steroid hormones : 6α-fluoro cortical hormones a new class of powerful corticoids

✍ Scribed by A. Bowers; E. Denot; M.Blanca Sanchez; H.L. Ringold

• Publisher: Elsevier Science
• Year: 1959
• Tongue: French
• Weight: 73 KB
• Volume: 1
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82756-8

✦ Synopsis

Incubation of 6u-fluoro-Reichstein's

Compound 3'" (I) and its A'-analog (IV) with bovine adrenals followed by acetylation led to 6c4uorohydrocortisone acetate (II) and 6a-fluoroprednisolone acetate (III) respectively. Selenium dioxide oxidation of II also afforded III. Chromium trioxide oxidation of II and 111 gave 6a-fluorocortisone acetate (VIIa) and 6a-fluoroprednisone acetate (VIIIa) respectively. An alternate, all-chemical synthesis of 6a-fluorocortisone acetate (VIIa) From cortisone acetate (V) is described.

Dehydration of 6a-fluorohydrocortisone acetate gavb 6a-fluoro-dour)-dehydro Compound '?I (XIV). Formation of the corresponding 9/?,1 l,%epoxide (XV) and reaction with hydrogen fluoride then gave 6a,9a_difluorohydrocortisone acetate (XVI) which afforded the prednisolone analog (XVII) upon oxidation with selenium dioxide.