Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1976-07-14
1977-10-11
Chan, Nicky
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260456R, C07D30906, C07C14368
Patent
active
040534863
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 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 a 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 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 ##STR2## wherein R.sub.6 is selected from the group consisting ##STR3## 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.
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Pelletier et al., J. Am. Chem. Soc., 90, 2889 (1968).
Chan Nicky
Gould George M.
Hoffmann-La Roche Inc.
Welt Samuel L.
Wittekind Raymond R.
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