Abstract:
Anordrin is a new oral steroidal contraceptive. During its systhesis a pair of epimers with different configuration of C
2 ethynyl groups is formed simutaneusly.The NMR of Anordrin and its related compounds was studied. The relative position in space between the C
2 ethynyl and the 19-CH
3 groups of the two epimers are different, thus the shielding effects of the ethynyl group on 19-CH
3 are not the same. The chemical shifts of 19-CH
3 of the two epimers and their hydrogenated compounds. are compared.The hydroxyl group of steroid formed a spcifically orientated complex with the solvent pyridine, hence the C
2 hydroxyl group of the parent compounds of the two epimers have different solvent shifts The chemical shifts of 19-CH
3 of their parent compounds in chloroform and pyridine were determined and compared.By means of the two methods mentioned above it is shown that the C
2 ethynyl of Anordrin is in
α-configuration.Pharmacologic test showed that the
β-form epimer has no antifertility effect.