ES307162A1 - A procedure of synthesis of steroid derivatives. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

A steroid derivative synthesis method characterized in that a lower alkyl ester of 5-oxo 6-heptenoic acid is condensed with 1,3-dioxo 2-and cyclopentane, here, and in the following, and an ethyl or an n-propyl, in the presence of an alkaline condensation agent, the condensation product is treated with an acid or with an acid-base pair, 1,5-dioxo 4- (2'-carboxy-ethyl) 7a is obtained -and 5, 6, 7, 7a-tetrahydro-indane, which is unfolded with the aid of an optically active base in its optical antipodes, the synthesis is continued on the dextrogiro isomer (in acetone), the ketone is reduced in position 1 of this last product with the help of a mixed hydride, is subjected to the reduced product, the 1 β -hydroxy 5-oxo 4- (2'-carboxy-ethyl) 7a β -and 6, 6, 7, 7a-tetrahydro-indane, or to an ester of acid lower than this to catalytic hydrogenation, proceeds in the case of a product to esterified in position 1 to a treatment with alkalis and the 1 β is obtained; -hydroxy 5-oxo 4- (2'-carboxy-ethyl) 7a β -and 3a α, 4 β 5, 6, 7, 7a-hexahydro-indane which is transformed with the aid of an anhydride or an acid chloride in δ -lactone from 1 β -OR '4- (2'-carboxy-ethyl) 5-hydroxy 7a β -and 3a α, 4 β 7, 7a-tetrahydro-indane, the latter is reacted with a 4-oxo pentyl magnesium halide whose ketone function is previously protected in the form of a ketal, the reaction product is treated with an alkaline agent, is then subjected to an acid hydrolysis, 3,5-dioxo 17 β is obtained; -hydroxy 13 β -and 4,5-dry 9 (10) -glyne, which is cyclized in the presence of an alkaline agent in 3-oxo 17 β -hydroxy 13 β -and 4,9 (10) -gonadiene, isomerized then this, after a previous esterification of the hydroxyl at 17, and 18-nor 13 β-and esterified estradiol is obtained which, if necessary, can be saponified according to the usual methods.