Richard J. Middleton
Expedient synthesis of a novel class of pseudoaromatic amino acids: Tetrahydroindazol-3-yl- and tetrahydrobenzisoxazol-3-ylalanine derivatives
Middleton, Richard J.; Mellor, Sarah L.; Chhabra, Siri Ram; Bycroft, Barrie W.; Chan, Weng C.
Authors
Sarah L. Mellor
Siri Ram Chhabra
Barrie W. Bycroft
Prof WENG CHAN WENG.CHAN@NOTTINGHAM.AC.UK
Professor of Chemical Biology
Abstract
A concise synthesis of novel homochiral aromatic amino acid surrogates comprising a tetrahydroindazole or a benzisoxazole system was developed via the acylation of a cyclic 1,3-diketone by the side-chain carboxyl functionality of either Boc-Asp-OtBu or Boc-Glu-OtBu followed by regioselective condensation with hydrazine, N-benzylhydrazine and hydroxylamine. The tetrahydroindazole nucleus was also constructed by the condensation of Boc-Asp-OtBu with the enamine, 1-pyrrolidino-1-cyclohexene followed by acid-hydrolytic treatment and reaction with hydrazines. Further functional group transformations gave N α-Fmoc-protected derivatives as useful building blocks for solid-phase peptide assembly. © 2003 Elsevier Ltd. All rights reserved.
Citation
Middleton, R. J., Mellor, S. L., Chhabra, S. R., Bycroft, B. W., & Chan, W. C. (2004). Expedient synthesis of a novel class of pseudoaromatic amino acids: Tetrahydroindazol-3-yl- and tetrahydrobenzisoxazol-3-ylalanine derivatives. Tetrahedron Letters, 45(6), 1237-1242. https://doi.org/10.1016/j.tetlet.2003.11.133
Journal Article Type | Article |
---|---|
Acceptance Date | Nov 27, 2003 |
Online Publication Date | Dec 13, 2003 |
Publication Date | Feb 2, 2004 |
Deposit Date | May 12, 2023 |
Journal | Tetrahedron Letters |
Print ISSN | 0040-4039 |
Electronic ISSN | 0040-4039 |
Publisher | Elsevier |
Peer Reviewed | Peer Reviewed |
Volume | 45 |
Issue | 6 |
Pages | 1237-1242 |
DOI | https://doi.org/10.1016/j.tetlet.2003.11.133 |
Public URL | https://nottingham-repository.worktribe.com/output/3137764 |
Publisher URL | https://www.sciencedirect.com/science/article/pii/S0040403903028983?via%3Dihub |
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