Steroids

An efficient synthesis of 4β-and 6α-hydroxylated bile acids

T Yoshimura, R Mahara, T Kurosawa, S Ikegawa…

Index: Yoshimura, Teruki; Mahara, Reijiro; Kurosawa, Takao; Ikegawa, Shigeo; Tohma, Masahiko Steroids, 1993 ,  vol. 58,  # 2  p. 52 - 58

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Citation Number: 15

Abstract

Abstract 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 ...