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

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

doi:10.1016/j.tetlet.2014.12.021

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 journal › Article › peer-review

Abstract

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 language	English
Article number	45545
Pages (from-to)	3123-3126
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	23
Early online date	13 Dec 2014
DOIs	https://doi.org/10.1016/j.tetlet.2014.12.021
Publication status	Published - 3 Jun 2015

Keywords

Ammonia
Artefact
Elaeokanidine
Indolizidine
Piperidone

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10.1016/j.tetlet.2014.12.021

Cite this

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

abstract = "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.",

keywords = "Ammonia, Artefact, Elaeokanidine, Indolizidine, Piperidone",

author = "Cuthbertson, {James D.} and Unsworth, {William P.} and Moody, {Catherine L.} and Taylor, {Richard J K}",

year = "2015",

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doi = "10.1016/j.tetlet.2014.12.021",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - The total synthesis of (+)-elaeokanidine A

T2 - natural product or isolation artefact?

AU - Cuthbertson, James D.

AU - Unsworth, William P.

AU - Moody, Catherine L.

AU - Taylor, Richard J K

PY - 2015/6/3

Y1 - 2015/6/3

N2 - 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.

AB - 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.

KW - Ammonia

KW - Artefact

KW - Elaeokanidine

KW - Indolizidine

KW - Piperidone

U2 - 10.1016/j.tetlet.2014.12.021

DO - 10.1016/j.tetlet.2014.12.021

M3 - Article

AN - SCOPUS:84933034777

SN - 0040-4039

VL - 56

SP - 3123

EP - 3126

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

M1 - 45545

ER -