ChemInform Abstract: Participation of the 19-Substituent in the Conversion of 19- Hydroxyandrost-4-ene-3,17-dione into the Corresponding 4,5-Diosphenol

Autor:	Sophia Hrycko, Peter Morand
Rok vydání:	2010
Předmět:	Reaction conditions Acetic acid chemistry.chemical_compound Chemistry Group (periodic table) Substituent General Medicine Medicinal chemistry Ene reaction
Zdroj:	ChemInform. 22
ISSN:	0931-7597
DOI:	10.1002/chin.199107218
Popis:	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.
Databáze:	OpenAIRE
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