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Chemical Synthesis of Rare Natural Bile Acids: 11α-Hydroxy Derivatives of Lithocholic and Chenodeoxycholic Acids.
- Source :
-
Lipids [Lipids] 2018 Apr; Vol. 53 (4), pp. 403-411. Date of Electronic Publication: 2018 Mar 09. - Publication Year :
- 2018
-
Abstract
- A method for the preparation of 11α-hydroxy derivatives of lithocholic and chenodeoxycholic acids, recently discovered to be natural bile acids, is described. The principal reactions involved were (1) elimination of the 12α-mesyloxy group of the methyl esters of 3α-acetate-12α-mesylate and 3α,7α-diacetate-12α-mesylate derivatives of deoxycholic acid and cholic acid with potassium acetate/hexamethylphosphoramide; (2) simultaneous reduction/hydrolysis of the resulting △ <superscript>11</superscript> -3α-acetoxy and △ <superscript>11</superscript> -3α,7α-diacetoxy methyl esters with lithium aluminum hydride; (3) stereoselective 11α-hydroxylation of the △ <superscript>11</superscript> -3α,24-diol and △ <superscript>11</superscript> -3α,7α,24-triol intermediates with B <subscript>2</subscript> H <subscript>6</subscript> /tetrahydrofuran (THF); and (4) selective oxidation at C-24 of the resulting 3α,11α,24-triol and 3α,7α,11α,24-tetrol to the corresponding C-24 carboxylic acids with NaClO <subscript>2</subscript> catalyzed by 2,2,6,6-tetramethylpiperidine 1-oxyl free radical (TEMPO) and NaClO. In summary, 3α,11α-dihydroxy-5β-cholan-24-oic acid and 3α,7α,11α-trihydroxy-5β-cholan-24-oic acid have been synthesized and their nuclear magnetic resonance (NMR) spectra characterized. These compounds are now available as reference standards to be used in biliary bile acid analysis.<br /> (© 2018 AOCS.)
Details
- Language :
- English
- ISSN :
- 1558-9307
- Volume :
- 53
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Lipids
- Publication Type :
- Academic Journal
- Accession number :
- 29520792
- Full Text :
- https://doi.org/10.1002/lipd.12013