Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids1)

Takashi Iida; Shinji Nishida; Frederic C. Chang; Toshifumi Niwa; Junichi Goto; Toshio Nambara

doi:10.1248/cpb.41.763

Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids¹⁾

Takashi Iida, Shinji Nishida, Frederic C. Chang, Toshifumi Niwa, Junichi Goto, Toshio Nambara

MED - Health Sciences

Research output: Contribution to journal › Article › peer-review

26 Citations (Scopus)

Abstract

A new method for the preparation of allochenodeoxycholic and allocholic acids is described. The key steps in the synthesis are 1) simultaneous oxidation-dehydrogenation reaction of 3a-hydroxy 5β-bile acid formyl esters with iodoxybenzene catalyzed by benzeneseleninic anhydride, 2) reductive allomerization at C-5 of the 1,4-dien-3-oxo hydroxy acids with lithium/liq. ammonia, and 3) subsequent reduction of the resulting 3-oxo 5α-compounds with K-Selectride.

Original language	English
Pages (from-to)	763-765
Number of pages	3
Journal	Chemical and Pharmaceutical Bulletin
Volume	41
Issue number	4
DOIs	https://doi.org/10.1248/cpb.41.763
Publication status	Published - 1993

Keywords

3α,7α,12α-trihydroxy-5α-cholanoic acid
3α,7α-dihydroxy-5α-cholanoic acid
bile acid

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.41.763

Cite this

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title = "Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids1)",

abstract = "A new method for the preparation of allochenodeoxycholic and allocholic acids is described. The key steps in the synthesis are 1) simultaneous oxidation-dehydrogenation reaction of 3a-hydroxy 5β-bile acid formyl esters with iodoxybenzene catalyzed by benzeneseleninic anhydride, 2) reductive allomerization at C-5 of the 1,4-dien-3-oxo hydroxy acids with lithium/liq. ammonia, and 3) subsequent reduction of the resulting 3-oxo 5α-compounds with K-Selectride.",

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T1 - Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids1)

AU - Iida, Takashi

AU - Nishida, Shinji

AU - Chang, Frederic C.

AU - Niwa, Toshifumi

AU - Goto, Junichi

AU - Nambara, Toshio

PY - 1993

Y1 - 1993

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AB - A new method for the preparation of allochenodeoxycholic and allocholic acids is described. The key steps in the synthesis are 1) simultaneous oxidation-dehydrogenation reaction of 3a-hydroxy 5β-bile acid formyl esters with iodoxybenzene catalyzed by benzeneseleninic anhydride, 2) reductive allomerization at C-5 of the 1,4-dien-3-oxo hydroxy acids with lithium/liq. ammonia, and 3) subsequent reduction of the resulting 3-oxo 5α-compounds with K-Selectride.

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KW - 3α,7α-dihydroxy-5α-cholanoic acid

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