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A Telescoped Route to 2,6-Disubstituted 2,3,4,5-Tetrahydropyridines and 2,6-syn-Disubstituted Piperidines: Total Synthesis of (−)-Grandisine G


  • We are grateful to the University of York for postdoctoral support (J.D.C.), and to Andrew A. Godfrey (AstraZeneca, Macclesfield) and Prof. Peter O’Brien (University of York) for valuable discussions. We also thank Dr. A. C. Whitwood (University of York) for the X-ray crystallographic data and Prof. A. R. Carroll (Griffith University, Brisbane) for comparison NMR spectroscopic data.


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A grand route to grandisines: A method for the conversion of 6-acyl cyclohexenones into 2,6-disubstituted 2,3,4,5-tetrahydropyridines and, after diastereoselective reduction, 2,6-syn-disubstituted piperidines has been developed. The scope of this process is outlined by the synthesis of cis-2-methoxycarbonylmethyl-6-pentylpiperidine and the first total synthesis of the Elaeocarpus-derived alkaloid (−)-grandisine G (see scheme).