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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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The article was received on 01 Jun 2016, accepted on 20 Jun 2016 and first published on 20 Jun 2016

Article type: Paper
DOI: 10.1039/C6OB01187J
Org. Biomol. Chem., 2016,14, 6826-6832

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    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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