Perbenzoic Acid Oxidation of Reichstein's “L” Acetate¹

Introduction of Oxygen into Ring B of Corticoids

“…This structure was proved by the following transformations: (1) reaction of V with hydriodic acid gave 1'4.6-androstatriene-3,11,17-trione (VI), a known compound1; (2) the latter, when treated with perphthalic acid, reverted to V; (3) degradation of 6a,7a-epoxy-17a,21-dihydroxy^1-4-pregnadiene-3,11,20-trione (lib) by sodium bismuthate21 also furnished V. Degradation of the side chain by peracids had been observed earlier. 22 was added, and the solution washed twice with 2.5 1. of saturated sodium carbonate solution. The latter was backextracted with methylene chloride, and the combined organic layers dried and concentrated.…”