Selective Hydrolysis and Oxidation of the Bismethylenedioxy Protective Group During Angular Methyl Migration in Corticosteroid Analogs

Autor:	Z. G. Hajos, G. R. Duncan, L. P. Makhubu
Rok vydání:	1974
Předmět:	Hydrolysis chemistry.chemical_compound chemistry medicine.drug_class Stereochemistry Organic Chemistry medicine Corticosteroid General Chemistry Catalysis Derivative (chemistry) Reaction product
Zdroj:	Canadian Journal of Chemistry. 52:1744-1749
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v74-251
Popis:	An attempt to achieve a 10β → 9β methyl migration in a 9,11α-epoxy-4,4-dimethylated derivative of cortisol (3) using BF3, failed to result in a clean reaction product. In contrast a 9α-amino-11-oxo derivative (9) rearranged smoothly to 20(R)-3β-acetoxy-9β-methyl-17α, 20-methylenedioxy-19-norpregn-5(10)-en-20-ol-11-one-21-oic acid (10) with sodium nitrite and acetic acid. During the migration, the protecting bismethylenedioxy group underwent selective hydrolysis and oxidation. The structure of the product has been established by i.r., n.m.r., and mass spectra analyses and a mechanism has been proposed for its formation. The product is an intermediate in the synthesis of 4,4-dimethylcucurbitacin and cortisol analogs, the goal of this chemical and biological investigation.
Databáze:	OpenAIRE
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