Nortestosterone progestins

Contraceptives. Figure 3 Examples of progestins derived from progesterone (pregnanes), 19-nortestosterone (estranes), and norgestrel (gonanes). 

The compound in which the 3-keto group is reduced to a hydrocarbon interestingly still acts as an orally active progestin. The preparation of this compound starts with the hydrolysis of dihydrobenzene (13-2) to afford 19-nortestosterone (15-1). Reaction with ethane-1,2-thiol in the presence of catalytic acid leads to the cyclic thioacetal (15-2). Treatment of this intermediate with Raney nickel in the presence of alcohol leads to the reduced desulfurized derivative (15-3). The alcohol at 17 is then oxidized by any of several methods, such as chromic acid in acetone (Jones reagent), and the resulting ketone (15-4) treated with hthium acetylide. There is thus obtained the progestin lynestrol (15-5) [18]. 

Hirsutism may also be aggravated by the "19-nortestosterone" derivatives, and combinations containing nonandrogenic progestins are preferred in these patients. 

Fig. 46.14. Progestins and norethisterone/norethindrone-related, 19-nortestosterone androstanes.

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