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Issue 28, 2016
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Synthesis of l-indospicine, [5,5,6-2H3]-l-indospicine and l-norindospicine

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Indospicine is a non-proteogenic amino acid that accumulates as the free amino acid in livestock grazing Indigofera plant species and causes both reproductive losses and hepatotoxic effects. An efficient synthetic route to L-indospicine from L-homoserine lactone is described. The methodology is applicable for the synthesis of both deuterium labelled isotopomers and structural analogues for utilisation in biological studies. The key steps are a zinc mediated Barbier reaction with acrylonitrile and a Pinner reaction that together introduce the target amidine moiety.

Graphical abstract: Synthesis of l-indospicine, [5,5,6-2H3]-l-indospicine and l-norindospicine

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Article information

01 Jun 2016
20 Jun 2016
First published
20 Jun 2016

Org. Biomol. Chem., 2016,14, 6826-6832
Article type

Synthesis of L-indospicine, [5,5,6-2H3]-L-indospicine and L-norindospicine

C. Lang, S. Wong, S. Chow, V. L. Challinor, K. W. L. Yong, M. T. Fletcher, D. M. Arthur, J. C. Ng and J. J. De Voss, Org. Biomol. Chem., 2016, 14, 6826
DOI: 10.1039/C6OB01187J

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