A PRACTICAL, GENERAL 3-COMPONENT COUPLING APPROACH TO PROSTAGLANDIN AND NON-PROSTAGLANDIN-RELATED SKELETA

Starting with a terminal alkyne, a one-pot, six-step sequence has been developed which results in prostaglandin and related skeleta in high. yields. The method involves a transmetalation between organozirconium and cuprate species, as well as another between a copper enolate and organozincate reagent. Only catalytic amounts of the cuprate are needed. A variety of cyclic and acyclic enones participate in these multiple couplings, demonstrating that the methodology applies to far more than just the prostaglandin nucleus.