A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues
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. T...
| Main Authors: | , , , |
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| Format: | Article |
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Royal Society of Chemistry
2014
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| Online Access: | https://eprints.nottingham.ac.uk/37546/ |
| _version_ | 1848795481971359744 |
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| author | Chen, Chou-Hsiung Genapathy, Sivaneswary Fischer, Peter M. Chan, Weng C. |
| author_facet | Chen, Chou-Hsiung Genapathy, Sivaneswary Fischer, Peter M. Chan, Weng C. |
| author_sort | Chen, Chou-Hsiung |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T19:32:47Z |
| format | Article |
| id | nottingham-37546 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:32:47Z |
| publishDate | 2014 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-375462020-05-04T16:55:18Z https://eprints.nottingham.ac.uk/37546/ A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues Chen, Chou-Hsiung Genapathy, Sivaneswary Fischer, Peter M. Chan, Weng C. 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. Royal Society of Chemistry 2014-10-22 Article PeerReviewed Chen, Chou-Hsiung, Genapathy, Sivaneswary, Fischer, Peter M. and Chan, Weng C. (2014) A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues. Organic and Biomolecular Chemistry, 12 (48). pp. 9764-9768. ISSN 1477-0539 http://dx.doi.org/10.1039/c4ob02107j doi:10.1039/c4ob02107j doi:10.1039/c4ob02107j |
| spellingShingle | Chen, Chou-Hsiung Genapathy, Sivaneswary Fischer, Peter M. Chan, Weng C. A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues |
| title | A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues |
| title_full | A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues |
| title_fullStr | A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues |
| title_full_unstemmed | A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues |
| title_short | A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues |
| title_sort | facile approach to tryptophan derivatives for the total synthesis of argyrin analogues |
| url | https://eprints.nottingham.ac.uk/37546/ https://eprints.nottingham.ac.uk/37546/ https://eprints.nottingham.ac.uk/37546/ |