- Participation of the 19-Substituent in the Conversion of 19-Hydroxyandrost-4-ene-3,17-dione into the Corresponding 4,5-Diosphenol
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The synthesis of 4,19-dihydroxyandrost-4-ene-3,17-dione from 19-hydroxy-4β,5-epoxy-5β-androstane-3,17-dione and from 4β,5,19-trihydroxy-5β-androstane-3,17-dione is described.Under various reaction conditions other products are obtained as a result of participation of the 19-hydroxy group to form cyclic ethers.The formation of two of these products, 4α,5-isopropylidene-3α-hydroxy-3β,19-epoxy-5α-androstan-17-one and 4α-hydroxy-4β,19-epoxy-5α-androstane-3,17-dione, can be avoided by treatment of the aforementioned trihydroxy dione with acetic acid in the presence of HCl.
- Hrycko, Sophia,Morand, Peter
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p. 2899 - 2904
(2007/10/02)
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