Synthesis of non-phenolic bisbenzocyclooctadiene lignan lactones and aporphinic alkaloids, by oxidative coupling with new agents in fluoro acid medium. IV

Article abstract of DOI:10.1016/S0040-4020(01)87949-7

A systematic study of oxidants used in fluoro acid medium allowed us to increase notably the number of efficient reagents for the non-phenolic oxidative coupling of lignan and alkaloid precursors. If dibenzylbutanolide had no methylenedioxyle group, Re₂O₇ and RuO₂.2H₂O were the most efficient. With a methylenedioxyle group, best results were obtained with Tl₂O₃, Mn(OAc)₃.2H₂O and Ce(OH)₄. Finally, aporphines were obtained with good yields with Ce(OH)₄, RuO₂.2H₂O and Fe(OH)(OAc)₂.