Literature DB >> 16930077

Expedient synthesis of threo-beta-hydroxy-alpha-amino acid derivatives: phenylalanine, tyrosine, histidine, and tryptophan.

David Crich1, Abhisek Banerjee.   

Abstract

An expedient synthesis of enantiomerically pure threo-beta-hydroxy-alpha-amino acid derivatives of phenylalanine, tyrosine, histidine, and tryptophan is described. The NBS-mediated radical bromination of the N,N-di-tert-butoxycarbonyl protected alpha-amino acids and subsequent treatment with silver nitrate in acetone provided the trans-oxazolidinones predominantly. Cesium carbonate catalyzed hydrolysis then generated the beta-hydroxy amino acid derivatives in excellent overall yield.

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Year:  2006        PMID： 16930077      PMCID： PMC2621330          DOI： 10.1021/jo061159i

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  15 in total

1.  Regioselective asymmetric aminohydroxylation approach to a beta-hydroxyphenylalanine derivative for the synthesis of ustiloxin D.

Authors:  H Park; B Cao; M M Joullié
Journal:  J Org Chem       Date:  2001-10-19       Impact factor: 4.354

Review 2.  Bleomycin: new perspectives on the mechanism of action.

Authors:  S M Hecht
Journal:  J Nat Prod       Date:  2000-01       Impact factor: 4.050

3.  Concise synthesis of all stereoisomers of beta-methoxytyrosine and determination of the absolute configuration of the residue in callipeltin A.

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Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

4.  Bouvardin and deoxybouvardin, antitumor cyclic hexapeptides from Bouvardia ternifolia (Rubiaceae).

Authors:  S D Jolad; J J Hoffmann; S J Torrance; R M Wiedhopf; J R Cole; S K Arora; R B Bates; R L Gargiulo; G R Kriek
Journal:  J Am Chem Soc       Date:  1977-11-23       Impact factor: 15.419

5.  Stereoselective synthesis of beta-hydroxyphenylalanines using imino 1,2-Wittig rearrangement of hydroximates.

Authors:  Okiko Miyata; Hiroshi Asai; Takeaki Naito
Journal:  Chem Pharm Bull (Tokyo)       Date:  2005-04       Impact factor: 1.645

6.  Studies on the total synthesis of tallysomycin. Synthesis of the threonylbithiazole moiety containing a structurally unique glycosylcarbinolamide.

Authors:  M L Sznaidman; S M Hecht
Journal:  Org Lett       Date:  2001-09-06       Impact factor: 6.005

7.  Determination of the structure of exochelin MN, the extracellular siderophore from Mycobacterium neoaurum.

Authors:  G J Sharman; D H Williams; D F Ewing; C Ratledge
Journal:  Chem Biol       Date:  1995-08

8.  Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening.

Authors:  Stephen C. Bergmeier; Dionne M. Stanchina
Journal:  J Org Chem       Date:  1997-06-27       Impact factor: 4.354

9.  Total synthesis of exochelin MN and analogues.

Authors:  Li Dong; Marvin J Miller
Journal:  J Org Chem       Date:  2002-07-12       Impact factor: 4.354

10.  New glycopeptide antibiotics. I. The structures of orienticins.

Authors:  N Tsuji; M Kobayashi; T Kamigauchi; Y Yoshimura; Y Terui
Journal:  J Antibiot (Tokyo)       Date:  1988-06       Impact factor: 2.649
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  4 in total

Review 1.  Conformationally constrained histidines in the design of peptidomimetics: strategies for the χ-space control.

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Journal:  Int J Mol Sci       Date:  2011-05-03       Impact factor: 5.923

2.  Novel Cinchona alkaloid derived ammonium salts as catalysts for the asymmetric synthesis of beta-hydroxy alpha-amino acids via aldol reactions.

Authors:  Bing Ma; Jared L Parkinson; Steven L Castle
Journal:  Tetrahedron Lett       Date:  2007-03-19       Impact factor: 2.415

3.  Concise Total Synthesis of (+)-Bionectins A and C.

Authors:  Alexis Coste; Justin Kim; Timothy C Adams; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2013-08       Impact factor: 9.825

4.  Realizing serine/threonine ligation: scope and limitations and mechanistic implication thereof.

Authors:  Clarence T T Wong; Tianlu Li; Hiu Yung Lam; Yinfeng Zhang; Xuechen Li
Journal:  Front Chem       Date:  2014-05-20       Impact factor: 5.221
  4 in total

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