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A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues

Chen, Chou-Hsiung; Genapathy, Sivaneswary; Fischer, Peter M.; Chan, Weng C.

Authors

Chou-Hsiung Chen

Sivaneswary Genapathy

Peter M. Fischer



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.

Citation

Chen, C., Genapathy, S., Fischer, P. M., & Chan, W. C. (2014). A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues. Organic and Biomolecular Chemistry, 12(48), 9764-9768. https://doi.org/10.1039/c4ob02107j

Journal Article Type Article
Acceptance Date Oct 22, 2014
Publication Date Oct 22, 2014
Deposit Date Oct 13, 2016
Publicly Available Date Oct 13, 2016
Journal Organic and Biomolecular Chemistry
Print ISSN 1477-0520
Electronic ISSN 1477-0539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 12
Issue 48
Pages 9764-9768
DOI https://doi.org/10.1039/c4ob02107j
Public URL http://eprints.nottingham.ac.uk/id/eprint/37546
Publisher URL http://dx.doi.org/10.1039/c4ob02107j
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

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