Novel Macrocyclic Bile Acid Derivatives; Selective and Easy Binding of Two Cholic Acid Moieties at the 3- and 3′-Positions

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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