Conversion of lanosterol into a compound with the carbon skeleton of fusidic acid
Abstract
A recently established method for the monodemethylation of triterpenes at C-4 has been used to convert lanosterol into 3β-acetoxy-9,11α-epoxy-4α, 14α-dimethyl-5α-cholestane. A boron trifluoride-catalysed ‘backbone’ rearrangement of this epoxide produced 3β-acetoxy-29-nor-8α, 14β-dammara-9(11), 13(17)-diene and 3β-acetoxy-4α, 14α-dimethyl-5α, 9β-cholestan-11-one.