In order to find new ways for the functionalization of the A and B rings of the steroid nucleus, the reaction of 5α-androst-2-en-17β-ol 17-acetate (1), cholesta-2,4-diene (4) and cholesta-4,6-dien-3β-ol 3-acetate (7) was examined using stoichiometric amounts of ruthenium tetraoxide to yield 1,2-cis diols and/or α-hydroxy ketones. The reaction of 5α-cholest-2-en-3-ol 3-acetate (9) with ruthenium tetraoxide was also carried out and afforded, apart from an α-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 / Musumeci, Domenica; Giovanni N., Roviello; Sica, Donato. - In: STEROIDS. - ISSN 0039-128X. - STAMPA. - 69:(2004), pp. 173-179. [10.1016/j.steroids.2003.11.003]
The oxidation of Delta2, Delta2,4 and Delta4,6 steroids with RuO4
MUSUMECI, DOMENICA;SICA, DONATO
2004
Abstract
In order to find new ways for the functionalization of the A and B rings of the steroid nucleus, the reaction of 5α-androst-2-en-17β-ol 17-acetate (1), cholesta-2,4-diene (4) and cholesta-4,6-dien-3β-ol 3-acetate (7) was examined using stoichiometric amounts of ruthenium tetraoxide to yield 1,2-cis diols and/or α-hydroxy ketones. The reaction of 5α-cholest-2-en-3-ol 3-acetate (9) with ruthenium tetraoxide was also carried out and afforded, apart from an α-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 | Dimensione | Formato | |
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