Syntheses of Racemic and Optically Active 13β-Ethylgonanes.

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Abstract
During the course of the synthesis of 18-methylestradiol 3-methyl ether, steric effect caused by the methyl group at 18-position was observed. Ethylenediamine was a good solvent for the ethynylation reaction of the hindered ketone. Racemic and optically active 17[beta]-hydroxy-13 , 17[alpha]-diethylgon-4-en-3-one were synthesized from 1-vinyl-6-methoxy-1-tetralol and 2-ethyl-1, 3-cyclopentanedion. The dextrorotatory diethylgonenone as well as the corresponding racemic diethylgonenone showed strong anabolic activities, whereas the levoro-tatory compound had no biological activity.

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