SYNTHESIS OF (+/-)-SENOXEPIN - THE FIRST NATURALLY OCCURING ANTI-HUECKEL OXEPIN DERIVATIVE

Article abstract of DOI:10.1016/S0040-4039(00)72725-0

The first total synthesis of (+/-)-senoxepin 3 is described. 3 is prepared via an intramolecular <4+2> cycloaddition from a substituted decadienyne 7.The resulting hexalin 8 was converted to a lactone, which on epoxidation, NBS bromination and elimination with NaI afforded senoxepin.