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Synthesis 1994; 1994(11): 1167-1170
DOI: 10.1055/s-1994-25665
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Facile Synthesis of 4-Piperidones by Condensation of an α,β-Unsaturated Ketone, an Aldehyde and Ammonia: Synthesis of the Dendrobatid Frog Alkaloid 241D

Michael W. Edwards* , H. Martin Garraffo, John W. Daly
  • *Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892-0820, USA
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Publikationsdatum:
25. April 2002 (online)

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A one-step reaction of an α,β-unsaturated ketone (3-penten-2-one, 1), an aldehyde (decanal, 2) and an amine (ammonia) afforded mainly the cis-isomer of (±)-2-methyl-6-nonyl-4-piperidone (3). Sodium borohydride reduction afforded as the major product (±)-cis,cis-4-hydroxy-2-methyl-6-nonylpiperidine (4), identical in NMR and IR spectra to the (+)-piperidine 241D isolated from skin extracts of a dendrobatid frog. The reaction was shown to be generally applicable for the synthesis of 2,6-disubstituted 4-piperidones.