Stereoselective synthesis of 3β-bile acid derivatives from the 3ga-analog

✍ Scribed by J.K. Denike; M. Moskova; X.X. Zhu

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 493 KB
• Volume: 77
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(95)02476-y

✦ Synopsis

The stereoselective transformation from the commonly occurring 3~-bile acids and derivatives to their 3fl-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 3fl-hydroxy epimer by the use of the Mitsunobu reaction and to a 3fl-amino cholic acid analog via a tosylation followed by a S,~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.