Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step

Article abstract of DOI:10.1021/ol0530326

Catalytic asymmetric allylation of 3,4-dihydro-6,7-dimethoxyisoquinoline was carried out using allyltrimethoxysilane in the presence of Cu(I) and tol-BINAP. The allyl adduct thus obtained was transformed to a chiral synthetic intermediate for (-)-emetine in good yield. The procedure was applied to the total synthesis of ent-emetine.