Reactions of epoxides—V : Rearrangements of 5,6-epoxy-6-methyl-cholestanes with boron trifluoride☆

Add time:08/23/2019    Source:sciencedirect.com

5,6,α-Epoxy-6β-methyl-5α-cholestane, like its 3β-acetoxy derivative, undergoes rearrangement with boron trifluoride to give the 5β-methyl-A-homo-B-nor-4a-ketone. The 3-deoxy-4a-ketone, however, undergoes a further rearrangement with boron trifluoride to give 5-methyl-5β-cholestan-6-one. 3β-Acetoxy-5,6β-epoxy-6α-methyl-5β-cholestane reacts rapidly with boron trifluoride to give a fluorohydrin, which suffers a slower rearrangement to give both the 5β-methyl-A-homo-B-nor-4a-ketone and 3β-acetoxy-5-methyl-5α-cholestan-6-one. In contrast, the 3-deoxy 5β,6β-epoxide gives 6-methyl-cholesta-3,5-diene, 5-acetyl-B-nor-5β-cholestane, and 5-methyl-5α-cholestan-6-one.

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