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
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 in questo prodotto:
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EurJOrgChem2001-MTO_H2O2urea.pdf
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