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Royal Society of Chemistry, Organic and Biomolecular Chemistry, 48(12), p. 9764-9768

DOI: 10.1039/c4ob02107j

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A Facile Approach to Tryptophan Derivatives for the Total Synthesis of Argyrin Analogues

Journal article published in 2014 by Chou-Hsiung Chen, Sivaneswary Genapathy, Peter M. Fischer ORCID, Weng C. Chan ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated were (S)-methylbenzylamine and related derivatives. To illustrate the robustness of the method, eight optically pure (S)-tryptophan analogues were synthesized, which were subsequently used for the convergent synthesis of a potent antibacterial agent, argyrin A and its analogues.