Abstract
Chemical evidence is presented in support of the structures assigned to the isomeric epoxides 4a and 5a obtained by peracid oxidation of the double bond in 3β-acetoxycholest-5-en-19-ol (2a). Reduction of 3β-acetoxy-5,6α-oxido-5α-cholestan-19-ol (4a) with lithium aluminum hydride leads exclusively to the C-5 alcohol while reduction of 3β-acetoxy-5,6β-oxido-5β-cholestan-19-ol (5a) with the same hydride results in the isolation of the C-5 and -6 alcohols in a ratio of 1:5. When an attempt was made to reduce the 5β,6β-epoxide 5a with lithium trimethoxyaluminohydride a rearrangement occurred. A structure is postulated for the compound isolated and a mechanism for its formation is discussed.
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