Steroids and related products. XLII. (1) The synthesis of 11-oxa steroids. IV. (2) The synthesis of 17,21-dihydroxy-11-oxa-4-pregene-3,20-dione, an 11-oxa analogue of the 17-hydroxylated glucocorticoids.
The synthesis, from 11-oxa-5alpha-pregnane-3,20-dione, available from hecogenin, of 17,21-dihydroxy-11-oxa-4-pregnene-3,20-dione, the first 11-oxa analogue of corticoid hormones, is described. The acetate of its 1-dehydro derivative, 17-hydroxy-21-acetoxy-1,4-pregnadiene-3,20-dione, analogous in structure to the acetates of prednisone and prednisolone, is an intermediate in the synthesis.
D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D011282:Pregnenediones / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis
D011282:Pregnenediones; D013260:Steroids, Heterocyclic; C012916:17,21-dihydroxy-11-oxa-4-pregnene-3,20-dione