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Dr. James D. Cuthbertson and Prof. Richard J. K. Taylor A Telescoped Route to 2,6-Disubstituted 2,3,4,5-Tetrahydropyridines and 2,6-syn-Disubstituted Piperidines: Total Synthesis of (−)-Grandisine G Angewandte Chemie International Edition 52

Version of Record online: 12 DEC 2012 | DOI: 10.1002/anie.201208118

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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).

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