The modified methods for obtaining biologically active D-seco derivatives of 5-androstene
2001
Penov-Gasi, K.M. | Stojanovic, S.Z. | Medic-Mijacevic, Lj.D. | Molnar-Gabor, D.A. | Pejanovic, V.M. | Sakac, M.N. (University of Novi Sad, Novi Sad (Yugoslavia). Faculty of Sciences, Institute of Chemistry)
The Beckmann fragmentation reaction of 3beta,17beta-dihydroxy-17alfa-methyl-16-oximino-5-androstene (2), 3beta,17beta-dihydroxy-17alfa-ethyl-16-oximino-5-androstene (3) and 3beta,17beta-dihydroxy-17alfa-phenyl-16-oximino-5-androstene (4), with the aid of p-toluenesulphonyl chloride and acetic anhydride was investigated. The aim was to examine the influence of reagents and reaction conditions on yields of fragmentation products 5-10, especially of the biologically active products 5 and 7. Fragmentation of compounds 2, 3 and 4 with p-toluenesulphonyl chloride in pyridine afforded D-seco derivatives 7, 9 and 10 in good yields. The reaction of the same compounds (2,3,4) with acetic anhydride is a suitable method for preparing the corresponding D-seco derivatives.
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