An Expeditious Stereoselective Synthesis of (-)-Pinidinone from Ethyl Acetoacetate

An expeditious stereoselective synthesis of a naturally occurring 2,6-disubstituted piperidine alkaloid, (-)-pinidinone, has been accomplished with an overall yield of 31% in total eight steps. The synthesis involves ethyl acetoacetate as the starting material and the stereoselective -aminoallylation of aldehyde with (S)-tert-butanesulfinamide, allyl bromide, and indium and Grubbs' olefin cross-metathesis as the pivotal steps.