Efficient synthesis of the taxane C ring by fragmentation reaction of a bicyclo[2.2.2]octane derivative

Article abstract of DOI:10.1016/S0040-4039(97)01069-1

Compounds 3, the C/D ring moiety of paclitaxel without a 7-hydroxyl group, and 4, the C ring moiety of O-cinnamoyltaxicin-I (2), were synthesized stereoselectively from methyl (E,S)-3(2,2-dimethyl- 1,3-dioxolan-4-yl)-2- pentenoate (5) using the fragmentation reaction of bicyclo[2.2.2]octane derivative 9 as a key step to give 10.