Chemistry and Physics of Lipids p. 261 - 267 (1995)
Update date:2022-08-11
Topics:
Denike
Moskova
Zhu
The stereoselective transformation from the commonly occurring 3α-bile acids and derivatives to their 3β-analogs is important for certain applications of these amphiphilic natural compounds, especially in the preparation of polymers. We report here the stereoselective conversion of methyl cholate to its 3β-hydroxy epimer by the use of the Mitsunobu reaction and to a 3β-amino cholic acid analog via a tosylation followed by a S(n)2 displacement with sodium azide and a hydrogenation of the azide group with overall yields of 86% and 78%, respectively. The preparation of the methacrylate and methacrylamide derivatives from these compounds is also described.
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