Carboalumination-Epoxide Ring Opening for the Formation of 1,4-Disubstituted （Z）-3,6-Alkadienols

Allylalumination of alkynes （i.e. forming Negishi＇s （Z）-alkenyl dialkylalane） followed by alkenylation of epoxides provides 1,4-disubstituted （Z）-3,6-alkadienols. The alkenylation can be facilitated by the presence of a neighbouring coordinating group in the epoxides. This ＂one-pot＂ approach has been successfully applied in the large-scale production of C 10--C 15 fragment of 9,10-didehydroepothilone D （a synthetic epothilone analog as an anti-cancer agent in phase 2 clinical trials）.