Syntheses of 22- and 23-Hydroxylated Bile Alcohols

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The syntheses of four new bile alcohols, 5β-cholestane-3α, 7α, 12α, 22α-tetrol, 5β-cholestane-3α, 7α, 12α, 22β-tetrol, 5β-cholestane-3α, 7α, 12α, 23α-tetrol, and 5β-cholestane-3α, 7α, 12α, 23β-tetrol, were described. The 22-hydroxy compounds were prepared from bisnorcholyl aldehyde by the Grignard reaction with 3-methylbutylmagnesium chloride. The 23-hydroxy compounds were prepared from norcholic acid by the condensation with diisobutylcadmium and the subsequent lithium aluminum hydride reduction of the resulting 3α, 7α, 12α-trihydroxy-5β-cholestan-23-one. One of the synthetic tetrols, 5β-cholestane-3α, 7α, 12α, 23β-tetrol was identical with a bile alcohol isolated from a patient with cerebrotendinous xanthomatosis.
社団法人日本薬学会の論文
1978-09-25