Steroids p. 52 - 58 (1993)
Update date:2022-08-04
Topics:
Yoshimura, Teruki
Mahara, Reijiro
Kurosawa, Takao
Ikegawa, Shigeo
Tohma, Masahiko
An efficient method for the preparation of 4β- and 6α-hydroxylated bile acids has been developed.It involved a highly stereoselective acetoxylation at the 4β and 6α positions of 3- and 7-oxo bile acids, respectively, with lead tetraacetate in the presence of boron trifluoride etherate in acetic acid.Reduction of the resulting α-acetoxy ketones with sodium borohydride or tert-butylamine borane complex, and alkaline hydrolysis, provided the desired bile acids in good yields. Keywords: sterols; bile acid; 4β-hydroxylated bile acid;6α-hydroxylated bile acid; acetoxylation; lead tetraacetate oxidation
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