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Issue 42, 2016
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A simple, modular synthesis of C4-substituted tryptophan derivatives

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Abstract

The modular and versatile synthesis of C4-substituted tryptophan derivatives by direct functionalization of easily available N-acetyl 4-boronate tryptophan methyl ester via transition metal-catalyzed and metal-mediated cross coupling reactions is described. The versatility of the chemistry is highlighted by the gram-scale synthesis of 4-boronated N-acetyl-tryptophan methyl ester and the rapid synthesis of C4-aryl, C4-alkyl, C4-cyano, C4-trifluoromethyl, C4-azido, and C4-hydroxy tryptophan derivatives. The utility of our methodology is illustrated through the quick approach to the tricyclic azepino indole skeleton embedded in many natural products.

Graphical abstract: A simple, modular synthesis of C4-substituted tryptophan derivatives

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Publication details

The article was received on 16 Aug 2016, accepted on 01 Oct 2016 and first published on 04 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01791F
Citation: Org. Biomol. Chem., 2016,14, 10095-10100
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    A simple, modular synthesis of C4-substituted tryptophan derivatives

    F. Bartoccini, S. Bartolucci, M. Mari and G. Piersanti, Org. Biomol. Chem., 2016, 14, 10095
    DOI: 10.1039/C6OB01791F

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