To examine the reactivity of conjugated diene steroids towards methyltrioxorhenium (MTO)-catalysed oxidation with the urea-hydrogen peroxide adduct (UHP) and its possible use in functionalization of the rings of the steroid nucleus, the reactions of the MTO/UHP system with cholesta-3,5-diene (4) and 5a-cholesta-7,9(11)-dien-3 beta -yl acetate (13) in aprotic solvents were investigated. The structures of all new steroids were verified on the basis of chemical evidence and interpretation of spectroscopic data including H-H COSY, HMBC, and HMQC experiments.
Reactivity of steroidal dienes towards the methyltrioxorhenium/H2O2-urea oxidation system: isolation and characterization of new oxygenated steroids / Sica, Donato; Musumeci, Domenica; Zollo, Franco; DE MARINO, Simona. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2001:19(2001), pp. 3731-3739. [10.1002/1099-0690(200110)2001:19<3731::AID-EJOC3731>3.0.CO;2-2]
Reactivity of steroidal dienes towards the methyltrioxorhenium/H2O2-urea oxidation system: isolation and characterization of new oxygenated steroids
SICA, DONATO;MUSUMECI, DOMENICA;ZOLLO, FRANCO;DE MARINO, SIMONA
2001
Abstract
To examine the reactivity of conjugated diene steroids towards methyltrioxorhenium (MTO)-catalysed oxidation with the urea-hydrogen peroxide adduct (UHP) and its possible use in functionalization of the rings of the steroid nucleus, the reactions of the MTO/UHP system with cholesta-3,5-diene (4) and 5a-cholesta-7,9(11)-dien-3 beta -yl acetate (13) in aprotic solvents were investigated. The structures of all new steroids were verified on the basis of chemical evidence and interpretation of spectroscopic data including H-H COSY, HMBC, and HMQC experiments.| File | Dimensione | Formato | |
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