ChemInform Abstract: Epimerization in Acid Degradation Products of Artemisinin.

✍ Scribed by S.-M. HUI; K.-S. NGO; G. D. BROWN

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 29 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199813157

✦ Synopsis

Epimerization in Acid Degradation Products of Artemisinin.

-Treatment of artemisinin (I) with acids provides either the cyclohexanedione degradation product (III), which represents a useful intermediate for biosynthetic studies of artemisinin, or a decalin system (VI) which has undergone epimerization at the 7-position (yields in g). It is established that the bulky 7-substituent in the epimerized decalin adopts a thermodynamically favoured axial conformation. Conversely, the natural, equatorial conformation is favoured in the cyclohexanedione. Reasons for the different conformational preference are discussed.