Intramolecular palladium-catalysed cross coupling; a direct route to γ-oxo-α,β-unsaturated macrocycles

Article abstract of DOI:10.1016/S0040-4020(01)90977-9

Intramolecular Pd⁰-catalysed cross coupling of structures terminating in an acyl chloride and a β-stannylalkenoate has provided a new and an efficient route to 10-20 membered γ-oxo-α,β-unsaturated macrolides. Both the Z and E-β-stannylalkenoates afforded identical macrocyclic products demonstrating that under the reaction conditions thermodynamic equilibration of the first formed cross coupled product was most probably occurring. The method has been used to synthesise the macrocylic framework of the antibiotic A26771B and norpatulolide B.