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

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

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.-H., 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: https://nottingham-repository.worktribe.com/output/737800
• Publisher URL: http://dx.doi.org/10.1039/c4ob02107j
• Contract Date: Oct 13, 2016