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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.

Journal Article Type Article
Publication Date Oct 22, 2014
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
APA6 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
DOI https://doi.org/10.1039/c4ob02107j
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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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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