Stereospecific total steroidal synthesis via substituted C/D-tra

Details Stereospecific total steroidal synthesis via substituted C/D-tra Stereospecific total steroidal synthesis via substituted C/D-tra

1974-06-24

1976-10-12

Schwartz, Gerald A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260338, 2603407, 2603409, 2603459, 260456A, 260470, 260475A, 260476C, 260481R, 260483, 260487, 260488B, 260566R, C07C11900

Patent

active

039857336

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 ##SPC1##
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 alkoxy-carbonyl, aryloxy-carbonyl, lower cycloalkyloxy-carbonyl, 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, carboxy-benzoyl, trifluoroacetyl and camphorsulfonyl
And reacting them 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 ##EQU1## wherein R.sub.6 is selected from the group CONSISTING OF ##EQU2## and 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-carbonyl-methylene, 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: 3321511 (1967-05-01), Los

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