摘要 |
Total synthesis of known progestationally active steroidal materials. The steroids can be synthesized depending on the particular starting reactants selected by employing as intermediates bicyclic compounds of the formula <IMAGE> IV wherein m is an integer having a value of 1 or 2; R4 is hydrogen or lower alkyl; Z is lower alkylenedioxy, CH(OR2 ) and carbonyl; R8 when taken alone is hydrogen; R9 when taken alone is lower alkoxycarbonyl, aryloxy-carbonyl, lower cycloalkyloxycarbonyl, carbonyl-halide, hydrogen, carboxy, formyl and methylene-X, where X is a leaving group and when taken together are methylene; with the proviso that when Z is carbonyl R8 when taken alone is hydrogen; R9 when taken alone is carbonyl halide, hydrogen, carboxy, formyl and methylene-X where X is a leaving group and when taken together are methylene and R2 is hydrogen, lower alkyl, lower alkoxy-lower alkyl, phenyl-lower alkyl, tetrahydropyranyl, lower alkanoyl, benzoyl, nitrobenzoyl, carboxy-lower alkanoyl, carboxybenzoyl, trifluoroacetyl and camphorsulfonyl AND REACTING THEN IN THE CASE WHERE R8 and R9 taken together are methylene or R8 is hydrogen and R9 is methylene-X with beta -keto esters and other analogs of the formula <IMAGE> V wherein R6 is selected from the group consisting of <IMAGE> lower alkyl; R7 is lower alkyl; R15 is selected from the group consisting of oxo, lower alkylenedioxy or (hydrogen and lower alkoxy); B is selected from the group consisting of lower alkoxy-carbonylmethylene, lower-aryloxy-carbonyl-methylene, cyanomethylene, lower alkyl sulfinyl-methylene, lower alkyl sulfonyl-methylene, and R25 and R26 are independently selected from the group consisting of hydrogen, hydroxyl and lower alkyl.
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