114577-01-4Relevant academic research and scientific papers
6,7-DIHYDROXY-6,7-DIHYDROCANRENONE ISOMERS: IMPROVED SYNTHESIS AND PROTON NMR STUDY
Tal, Daniel M.
, p. 113 - 122 (1989)
The synthesis in improved yields of one 6,7-epoxide and three 6,7-dihydroxycanrenone derivatives is described.Canrenone was the starting material for all derivatives and was obtained by acid-catalyzed lactonization of potassium canrenoate.The epoxidation of canrenone to 6α,7α-epoxycanrenone by m-chloroperbenzoic acid was improved by addition of a free radical inhibitor.This epoxide was efficiently cleaved to 6β,7α-dihydroxy-6,7-dihydrocanrenone by perchloric acid in a dioxane-water mixture; 6β,7β- and 6α,7α-dihydroxy-6,7-dihydrocanrenone were obtained by OsO4 oxidation of canrenone in ether-pyridine and subsequent reduction of the osmates by hydrogen sulfide.The stereochemistry of the products obtained from the reaction of osmium tetroxide with the 6,7-double bond of steroidal 4,6-dien-3-ones has been a controversial issue for some time.A detailed proton-NMR study of the three diol derivatives unequivocally confirmed the proposed stereochemical structure.
Improved Synthesis of 6β,7β-Epoxy-17β-hydroxy-3-oxo-4,6-pregnadiene-21-carboxylic Acid γ-Lactone
Reinholz, Erhard,Vogler, Fritz
, p. 1015 - 1016 (2007/10/02)
The title compound 2, a metabolite of canrenone (1) in rats, is synthesized starting from 1 via derivative 3c in a 25-g scale in a much shorter time and higher yield than in the literature cited.
