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11-Oxygenated Steroids. I. Partial Syntheses of 11-Ketotestosterone and of Adrenosterone

โœ Scribed by Herzog, Hershel L.; Jevnik, Margaret A.; Perlman, Preston L.; Nobile, Arthur; Hershberg, E. B.

Book ID
115493252
Publisher
American Chemical Society
Year
1953
Tongue
English
Weight
523 KB
Volume
75
Category
Article
ISSN
0002-7863

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Conjugate 1,4-addition of 1- [(tert-butyldimethylsilyl)oxy]-2-methyl-1,3-cyclohexadiene (5) to 2-methylcyclopentenone in highly polar media and subsequent alkylation of the resultant silyl enol ether (4) with phenylthiodienyl carbonate I0 in 5.0 M LiC104.Et20 provides substrate 2. Exposure of 2 to T