Journal of Organic Chemistry p. 3265 - 3267 (1981)
Update date:2022-08-05
Topics:
Anastasia, Mario
Allevi, Pietro
Fiecchi, Alberto
Scala, Antonio
The epoxidation of 3β-acetoxy-5α-cholesta-8,14-diene with 1 molar equiv of m-chloroperbenzoic acid has been found useful for the synthesis of 15-oxygenated sterols.The major product of the reaction, 3β-acetoxy-14α,15α-epoxy-5α-cholest-8-ene, is decomposed on silica to a (1:1) mixture of 3β-acetoxy-5α-cholesta-8(14),9(11)-dien-15α-ol and 3β-acetoxy-5α-cholest-8(14)-ene-9α,15α-diol.The minor product obtained in the epoxidation is 3β-acetoxy-8α,9α-epoxy-5α-cholest-14-ene.
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Doi:10.1246/cl.1981.197
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