D-Norgestrel

CD curves for testosterone phenylpropionate in four different solvents are shown in Figure 6. Curves for the other compounds, testosterone, methyltestosterone, different testosterone esters, nandrolone phenylpropionate, norethisterone, and d-norgestrel, are essentially coincident with those in Fig. 6. The figure also demonstrates well how an increase in solvent polarity leads to a... 

In a beautifully straightforward synthesis5 of D-norgestrel (16) (Scheme 3) the key reaction is the transformation of dextrorotatory (13b) into (14) (85%) with paraformaldehyde and benzenesulphinic acid in triethanolamine-acetic acid. To avoid dialkylation at least a 3 1 volume ratio of triethanolamine to acetic acid is needed. Catalytic reduction to (15) followed by reaction with the anion of (5) yielded (6b X = O). Further elaboration produced dextrorotatory norgestrel (16). Monoalkylation of the diones (13) with l,3-dichlorobut-2-ene yields6 the compounds (17) and then, after steps, the laevorotatory ketones (18). 

Weiner, E. Victor, A. Johansson, E.D. Plasma levels of D-norgestrel after oral administration. Contraception 1976, 14 (5), 563-570. 

RP Blye, et al. Development and use of a radioimmunoassay for D-(—)-norgestrel 17-beta-cyclo-pentanecarboxylate. Steroids 48 27, 1986. 

TG Watson, et al. A sensitive direct radioimmunoassay for assessing D-norgestrel levels in human plasma. Ann Clin Biochem 25 280, 1988. 

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