An improved synthesis of 18-nor-17-ketosteroids and application of the method for the preparation of (3β,5β,13α)- and (3β,5β,13β)-3-hydroxygonan-17-one

Journal of Organic Chemistry

Volumn 61, Issue 21, 1996, Pages 7614-7616

  Han, Mingcheng ^a   Covey, Douglas F ^a  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

17 OXOSTEROID; 3 HYDROXYGONAN 17 ONE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029904975     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9611430     Document Type: Article

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19. 1/2 ≈ 12 Hz), assigned as the equatorial H-2 resonance, is observed at δ 2.79 in compound 9a. This resonance has a line shape very similar to the line shape of the equatorial H-3 proton in 5α-reduced 3α-hydroxysteroids. The axial H-2 resonance in compound 9b occurs above δ 2.5 and is obscured by overlapping multiplets.