Journal of the American Chemical Society, Vol.116, No.26, 11689-11702, 1994
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.
Keywords:CATALYZED CONJUGATE ADDITION;TRIPLY CONVERGENT SYNTHESIS;HIGHER-ORDER;ORGANIC-SYNTHESIS;ALPHA;BETA-UNSATURATED KETONES;TRANSMETALATION REACTIONS;ORGANOMETALLIC COMPOUNDS;ZINC HOMOENOLATE;ACID-CHLORIDES;REAGENTS