Synthesis of Cyclocaric Acid A and Comparison to Material fromCyclocarya paliurus

Matthew E. Wright, Jonathan Byrd, Chunnian He, and Norma Dunlap

Abstract

Components previously reported from Cyclocarya paliurus include the oleananes cyclocaric acids A and B, with cyclocaric acid A possessing an oxetane ring. Isolation of cyclocaric acid A from the plant extract and comparison to the literature report show that the compound originally reported as cyclocaric acid A is, in fact, hederagenin. This was confirmed by independent synthesis of the oxetane and indicates that cyclocaric acid A may not actually be a natural product.

 Hederagenin was purchased from Biopurify Phytochemicals (Chengdu, Sichuan, China)