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

25 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

Fingerprint Dive into the research topics of 'Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids<sup>1)</sup>'. Together they form a unique fingerprint.

Cite this

@article{9f08cc31e5a14d9c88d159fcf4c66a10,

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.",

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

author = "Takashi Iida and Shinji Nishida and Chang, {Frederic C.} and Toshifumi Niwa and Junichi Goto and Toshio Nambara",

year = "1993",

doi = "10.1248/cpb.41.763",

language = "English",

volume = "41",

pages = "763--765",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "4",

}

TY - JOUR

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

N2 - 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.

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.

KW - 3α,7α,12α-trihydroxy-5α-cholanoic acid

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

KW - bile acid

UR - http://www.scopus.com/inward/record.url?scp=0027230561&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027230561&partnerID=8YFLogxK

U2 - 10.1248/cpb.41.763

DO - 10.1248/cpb.41.763

M3 - Article

AN - SCOPUS:0027230561

VL - 41

SP - 763

EP - 765

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 4

ER -