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  • Title: Preparation and reactions of norethynodrel epoxide. A possible mechanism for A-ring aromatization of 19-norsteroids.
    Author: Thompson RM, Horning EC.
    Journal: Steroids Lipids Res; 1974; 5(3):133-42. PubMed ID: 4450215.
    Abstract:
    A 10beta-hydroxysteroid derivative of norethynodrel was synthesized through a 5,10-epoxide intermediate. During thin-layer chromatography, it is readily transformed into a 10-hydroxy compound (17-ethynyl-4-estren-10beta, 17beta-diol-3-one). Gas phase studies of derivatives of the 10-hydroxy compound demonstrated tha aromatization during silylation to 17alpha-ethynyl-estradiol-ditrimethysilyl ether will results if the 3-keto function has not been previously derived. Epoxidation may participate in the aromatization of the A-ring of 19-norsteroids to produce estrogens, and also may be involved in the in vivo conversion of norethynodrel to a 10beta-hydroxy steroid.
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