The oxidation of Delta2, Delta2,4 and Delta4,6 steroids with RuO4.
In order to find new ways for the functionalization of the A and B rings of the steroid nucleus, the reaction of 5alpha-androst-2-en-17beta-ol 17-acetate (1), cholesta-2,4-diene (4) and cholesta-4,6-dien-3beta-ol 3-acetate (7) was examined using stoichiometric amounts of ruthenium tetraoxide to yield 1,2-cis diols and/or alpha-hydroxy ketones. The reaction of 5alpha-cholest-2-en-3-ol 3-acetate (9) with ruthenium tetraoxide was also carried out and afforded, apart from an alpha-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.
Musumeci
Domenica
D
Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli "Federico II", Complesso Universitario Monte Sant'Angelo, Via Cinthia, I-80126 Napoli, Italy.
Roviello
Giovanni N
GN
Sica
Donato
D
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010084:Oxidation-Reduction; D017975:Ruthenium Compounds / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013256:Steroids / Q000737:chemistry*
D017975:Ruthenium Compounds; D013256:Steroids; C027646:ruthenium tetraoxide