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

Organic & Biomolecular Chemistry Pub Date: 2004-01-29 DOI: 10.1039/B312964K

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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