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Issue 5, 2004
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Synthesis of the 2,3,4-trisubstituted indole fragments of nosiheptide and glycothiohexide

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Abstract

Two routes to the protected 4-hydroxymethyl-3-methylindole-2-carboxylate fragment 17 of the thiopeptide antibiotic nosiheptide are described starting from methyl 4-methylindole-2-carboxylate 11, itself prepared in two steps, or from 3-amino-4-chlorobenzoic acid 26. The first route can be adapted to the synthesis of a fragment of the related antibiotic glycothiohexide-α, the 3,4-bis(hydroxymethyl)indole-2-carboxylate in which the two hydroxymethyl groups are differentiated as in indole 19 or the lactone 20.

Graphical abstract: Synthesis of the 2,3,4-trisubstituted indole fragments of nosiheptide and glycothiohexide

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Publication details

The article was received on 16 Oct 2003, accepted on 12 Dec 2003 and first published on 29 Jan 2004


Article type: Paper
DOI: 10.1039/B312964K
Org. Biomol. Chem., 2004,2, 701-708

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    Synthesis of the 2,3,4-trisubstituted indole fragments of nosiheptide and glycothiohexide

    D. J. Bentley, J. Fairhurst, P. T. Gallagher, A. K. Manteuffel, C. J. Moody and J. L. Pinder, Org. Biomol. Chem., 2004, 2, 701
    DOI: 10.1039/B312964K

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