Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1976-07-14
1978-03-07
Love, Ethel G.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
C07D31772
Patent
active
040779831
ABSTRACT:
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 ##STR1## wherein m is an integer having a value of 1 or 2; R.sub.4 is hydrogen or lower alkyl; Z is lower alkylenedioxy, CH(OR.sub.2 ) and carbonyl; R.sub.8 when taken alone is hydrogen; R.sub.9 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 R.sub.8 when taken alone is hydrogen; R.sub.9 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 R.sub.2 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 R.sub.8 and R.sub.9 taken together are methylene or R.sub.8 is hydrogen and R.sub.9 is methylene-X with .beta.-keto esters and other analogs of the formula ##STR2## wherein R.sub.6 is selected from the group consisting of ##STR3## lower alkyl; R.sub.7 is lower alkyl; R.sub.15 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 R.sub.25 and R.sub.26 are independently selected from the group consisting of hydrogen, hydroxyl and lower alkyl.
REFERENCES:
patent: 3417105 (1966-04-01), Hughes et al.
patent: 3576006 (1971-04-01), Saucy
patent: 4017545 (1977-04-01), Sauer et al.
Index Chem. 30, 246, (1968), No. 98642.
Gould George M.
Hoffmann-La Roche Inc.
Love Ethel G.
Welt Samuel L.
Wittekind Raymond R.
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