Development of modified Pauson-Khand reactions with ethylene and utilisation in the total synthesis of (+)-taylorione

Article abstract of DOI:10.1016/0040-4020(96)00259-1

Two complementary Pauson-Khanol annulation protocols for use with the gaseous alkene, ethylene, are described. These N-oxide promoted reactions (10 examples) are shown to proceed under both mild autoclave condition or, more conveniently, at atmospheric pressure. The developed methodology has been utilised as the key transformation in the total synthesis of the sesquiterpene (+)-taylorione which has been realised in a good overall yield from readily available (+)-2-carene.