The total synthesis of (+)-elaeokanidine A: natural product or isolation artefact?

James D. Cuthbertson, William P. Unsworth, Catherine L. Moody, Richard J K Taylor*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Abstract The first total synthesis of (+)-elaeokanidine A is reported. The synthesis features a formic acid-mediated cyclisation to access the indolizidine core and a double conjugate addition of ammonia to construct the piperidone unit. On the basis of 1H NMR spectroscopic data, the relative stereochemistry of elaeokanidine A has been confirmed. Two isomeric species were also formed during the piperidone ring construction, which are potentially elaeokanidines B and C, although their structures could not be assigned unambiguously. The synthetic transformations used to prepare these products are analogous to conditions employed during the extraction procedure, raising questions about the true origins of these compounds.

Original languageEnglish
Article number45545
Pages (from-to)3123-3126
Number of pages4
JournalTetrahedron Letters
Issue number23
Early online date13 Dec 2014
Publication statusPublished - 3 Jun 2015


  • Ammonia
  • Artefact
  • Elaeokanidine
  • Indolizidine
  • Piperidone

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