In order to find new ways for the functionalization of the A and B rings of the steroid nucleus, the reaction of 5-androst-2-en-17-ol 17-acetate (1), cholesta-2,4-diene (4) and cholesta-4,6-dien-3-ol 3-acetate (7) was examined using stoichiometric amounts of ruthenium tetraoxide to yield 1,2-cis diols and/or -hydroxy ketones. The reaction of 5-cholest-2-en-3-ol 3-acetate (9) with ruthenium tetraoxide was also carried out and afforded, apart from an -hydroxy ketone, also a diketone and a seco-dicarboxylic acid. The structures of all new steroids, including stereochemical details, were deduced by analysis of spectral data.
The oxidation of Delta2, Delta2,4 and Delta4,6 steroids with RuO4
2004
Abstract
In order to find new ways for the functionalization of the A and B rings of the steroid nucleus, the reaction of 5-androst-2-en-17-ol 17-acetate (1), cholesta-2,4-diene (4) and cholesta-4,6-dien-3-ol 3-acetate (7) was examined using stoichiometric amounts of ruthenium tetraoxide to yield 1,2-cis diols and/or -hydroxy ketones. The reaction of 5-cholest-2-en-3-ol 3-acetate (9) with ruthenium tetraoxide was also carried out and afforded, apart from an -hydroxy ketone, also a diketone and a seco-dicarboxylic acid. The structures of all new steroids, including stereochemical details, were deduced by analysis of spectral data.File in questo prodotto:
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