Stereoselective epoxidation of 4(20)-exomethylene in taxinine derivatives and assignment of the epoxide orientation by NMR

Article abstract of DOI:10.1016/S0040-4020(98)00018-0

Epoxidation of taxinine (1), taxinine A (2), and taxinine derivative 7 with m-chloroperbenzoic acid afforded the α-4(20)-epoxides selectively (α:β = 99:1), while epoxidation of taxinine derivatives 7 and 8 with dimethyldioxirane gave the β-4(20)-epoxides