Bh. Lipshutz et Mr. Wood, A PRACTICAL, GENERAL 3-COMPONENT COUPLING APPROACH TO PROSTAGLANDIN AND NON-PROSTAGLANDIN-RELATED SKELETA, Journal of the American Chemical Society, 116(26), 1994, pp. 11689-11702
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 neede
d. A variety of cyclic and acyclic enones participate in these multipl
e couplings, demonstrating that the methodology applies to far more th
an just the prostaglandin nucleus.