A HIGHLY EFFICIENT SYNTHESIS OF (-)-PINIDINOL

摘要

A short step synthesis of the bioactive piperidine alkaloid (-)-pinidinol was achieved using a cross metathesis and a reductive amination as the key steps. North American conifers of the Pinaceae family have shown to contain several biologically active 2,6-disubstituted piperidine alkaloids of particular ecological importance. Although (-)-pinidinol (1) exhibits interesting antifeedant activity against Eastern spruce budworms, only three enantioselective syntheses have been described, two of which suffer from lengthy procedures and low overall yields.