✦ LIBER ✦

Reactivity of Steroidal Dienes towards the Methyltrioxorhenium/H2O2−Urea Oxidation System: Isolation and Characterization of New Oxygenated Steroids

✍ Scribed by Donato Sica; Domenica Musumeci; Franco Zollo; Simona De Marino

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 313 KB
Volume: 2001
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200110)2001:19<3731::aid-ejoc3731>3.0.co;2-2

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✦ Synopsis

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 5α-cholesta-7,9(11)-dien-3β-yl acetate (13) in aprotic solvents were investigated. These oxidations were performed both at 0 °C and at 25 °C, in either CHCl 3 or diethyl ether as solvents, and in the presence of pyridine as ligand.