Issue 5, 2004

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

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

Article information

Article type
Paper
Submitted
16 Oct 2003
Accepted
12 Dec 2003
First published
29 Jan 2004

Org. Biomol. Chem., 2004,2, 701-708

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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