PROCESS FOR PRODUCING DELTA-9-BRACKET-11-BRACKET CLOSED-ABOVE-5-ALPHA-D-HOMO-20-OXO-STEROIDES

摘要

3 alpha -Hydroxy and 3 alpha -acyloxy- DELTA 9(11)-5 alpha -D-homo-20-ketopregnenes of the formula wherein R is hydrogen or acyl, R1 is hydrogen or methyl and R2 is methyl or ethyl, are produced by esterifying a corresponding 3 beta -hydroxy-5 alpha -20-keto pregnane of the formula wherein R1 and R2 have the values given above, with m-iodo-benzoic acid with inversion of the 3 beta -oxy group to a 3 alpha -oxy group; chlorinating the thus-produced 3 alpha -m-iodobenzoyl ester with dichloroiodobenzene under irradiation; and treating the reaction product with a dehydrohalogenating silver salt. Optionally thereafter, the 3 alpha -iodobenzoyl group is split off in a conventional manner to produce the corresponding 3 alpha -hydroxy steroid and optionally the thus-produced 3 alpha -hydroxy steroid is esterified to produce a desired 3-ester thereof.