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Synthesis 2009(24): 4175-4182
DOI: 10.1055/s-0029-1217057
DOI: 10.1055/s-0029-1217057
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Novel Macrocyclic Bile Acid Derivatives; Selective and Easy Binding of Two Cholic Acid Moieties at the 3- and 3′-Positions
Further Information
Received
22 June 2009
Publication Date:
19 October 2009 (online)
Publication History
Publication Date:
19 October 2009 (online)
Abstract
The synthesis of macrocyclic derivatives of bile acids (cholaphanes) is elaborated using the formation of ester or amide linkages at the 3α,3′α- and 24,24′-positions of lithocholic, deoxycholic or cholic acids. The conditions were found under which the selective diacylation at the 3α,3′α- and 24,24′-positions of two molecules of cholic acid by dichloroanhydrides of arene(hetarene)dicarboxylic acid proceeds in good yields without prior protection of the 7α- and 12α-hydroxy groups.
Key words
macrocycles - bile acids - cyclophanes - cholaphanes - cyclizations
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