Palladium Catalysed Cross-Coupling of Vinyl Triflates with 9-Alkyl-9-borobicyclononanes. Total Synthesis of (-)-Isoseiridine.

Article abstract of DOI:10.1016/S0040-4020(01)80703-1

Pd(O) Catalysed cross-coupling of butenolide-3-triflates to 9-alkyl-9-borobicyclo<3.3.1>nonanes occurs in moderate to good yield and tolerates a range of functionality.Application of this methodology combined with addition of diethylzinc to a butenolide aldehyde in the presence of an ephedrine derivative leads to a 3-step synthesis of (-)-isoseiridine with 88percent e.e. in good yield.