Asymmetric epoxidation of digeranyl by cultured cells of Nicotiana tabacum

Abstract Asymmetric epoxidation of digeranyl, which is a squalene analog, with cultured cells of Nicotiana tabacum was investigated. Feeding of [8‐3H]‐digeranyl into the cultured cells of N. tabacum resulted in the formation of (3S)‐2,3‐epoxydigeranyl and 6,7‐epoxydigeranyl. It was found that the epoxidation of digeranyl with N. tabacum was highly stereoselective. Copyright © 2003 John Wiley & Sons, Ltd.