Document Detail


Synthesis of four diastereoisomers at carbons 24 and 25 of 3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestan-26-oic acid, intermediates of bile acid biosynthesis.
MedLine Citation:
PMID:  6631226     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The synthesis of four stereoisomers at C-24 and C-25 of 3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestan-26-oic acid is described. Pyridium chlorochromate oxidation of 3 alpha,7 alpha,12 alpha-triacetoxy-5 beta-cholan-24-ol (II) prepared from cholic acid (I) afforded 3 alpha,7 alpha,12 alpha-triacetoxy-5 beta-cholan-24-al (III) which was converted to a mixture of the four stereoisomers (IV-VII) by a Reformatsky reaction with ethyl DL-alpha-bromopropionate followed by alkaline hydrolysis. Separation of these isomers (IV-VII) was achieved by silica gel column chromatography, and subsequent reversed-phase partition column chromatography. The configurations at C-24 were elucidated by conversion of each isomer into (24R)- or (24S)-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24-tetrol (XII or XI) by Kolbe electric coupling, the C-24 configurations of which were determined by modified Horeau's method and 13C-nuclear magnetic resonance spectroscopy. The stereochemistries at C-25 were deduced by comparison of IV-VII with the products of the hydroboration followed by oxidation with alkaline hydrogen peroxide of (24E)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholest-24-en-26-oic acid (XIII).
Authors:
M Une; F Nagai; K Kihira; T Kuramoto; T Hoshita
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of lipid research     Volume:  24     ISSN:  0022-2275     ISO Abbreviation:  J. Lipid Res.     Publication Date:  1983 Jul 
Date Detail:
Created Date:  1983-12-17     Completed Date:  1983-12-17     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0376606     Medline TA:  J Lipid Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  924-9     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Bile Acids and Salts / biosynthesis*
Chemical Phenomena
Chemistry
Cholestanols / chemical synthesis*,  isolation & purification
Chromatography / methods
Stereoisomerism
Chemical
Reg. No./Substance:
0/Bile Acids and Salts; 0/Cholestanols; 1061-64-9/3,7,12,24-tetrahydroxycholestanoic acid

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