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Communication | Special issue | Vol 82, No. 2, 2010, pp.1119-1125
Published online, 12th August, 2010
DOI: 10.3987/COM-10-S(E)83
Modification of D-Ring Moiety of Steroids − A Novel Palladium Catalyzed Baeyer-Villiger Type Rearrangement of Cyclic Silylenol Ether Derivatives

Minoru Tamiya,* Futa Takada, Nobuhisa Isaka, Nahoko Iimura, and Masaji Ishiguro*

*Chemical Biology Laboratory, Department of Applied Life Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Niigata 956-8603, Japan


A novel Baeyer–Villiger type rearrangement reaction of cyclic silylenol ether derived from dehydroepiandrosterone via oxygen and catalytic amount of palladium acetate in the presence of DMSO has been developed. The reaction proceeded at low temperature and high pressure of oxygen to afford corresponding α,β-unsaturated lactones in moderate yields.