Literature DB >> 20011098

Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct.

Weiqiang Huang1, Marvin J Miller.   

Abstract

O-TBS-protected methyl trans-4-hydroxypyroglutamate and methyl trans-4-hydroxyproline ester were synthesized from nitroso-cyclopentadiene Diels-Alder cycloadducts. Enzymatic resolution of the key intermediate, 4-amino-cyclopent-2-enol, provides access to both L- and D- amino acids.

Entities:  

Year:  2008        PMID： 20011098      PMCID： PMC2662620          DOI： 10.1016/j.tetasy.2008.12.013

Source DB:  PubMed          Journal:  Tetrahedron Asymmetry        ISSN： 0957-4166


  31 in total

1.  Synthesis of enantiomerically and diastereomerically pure 2(S)-amino-6(R)-hydroxy-1,7-heptanedioic acid dimethyl ester hydrochloride from cycloheptadiene.

Authors:  B T Shireman; M J Miller
Journal:  J Org Chem       Date:  2001-07-13       Impact factor: 4.354

2.  An Efficient Synthesis of cis- and trans-Methyl-3-hydroxy-2-pyrrolidone- 5-carboxylates, Key Intermediates for the Synthesis of gamma-Substituted Glutamic Acid Analogs.

Authors:  Lawrence J. Heinz; W. H. W. Lunn; R. E. Murff; Jonathan W. Paschal; Larry A. Spangle
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

Review 3.  Physiological and pathophysiological roles of excitatory amino acids during central nervous system development.

Authors:  J W McDonald; M V Johnston
Journal:  Brain Res Brain Res Rev       Date:  1990 Jan-Apr

4.  The synthesis and in vitro testing of structurally novel antibiotics derived from acylnitroso Diels-Alder adducts.

Authors:  George P Nora; Marvin J Miller; Ute Möllmann
Journal:  Bioorg Med Chem Lett       Date:  2006-05-26       Impact factor: 2.823

5.  The synthesis of (-)-isodomoic acid C.

Authors:  Jonathan Clayden; Faye E Knowles; Ian R Baldwin
Journal:  J Am Chem Soc       Date:  2005-03-02       Impact factor: 15.419

6.  Collagen stability: insights from NMR spectroscopic and hybrid density functional computational investigations of the effect of electronegative substituents on prolyl ring conformations.

Authors:  Michele L DeRider; Steven J Wilkens; Michael J Waddell; Lynn E Bretscher; Frank Weinhold; Ronald T Raines; John L Markley
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

7.  Regio- and stereochemically controlled formation of hydroxamic acid containing anti- or syn-1,4-cycloalkenols from acylnitroso-derived Diels-Alder adducts.

Authors:  M D Surman; M J Miller
Journal:  J Org Chem       Date:  2001-04-06       Impact factor: 4.354

8.  Chemoenzymatic synthesis and synthetic application of enantiopure aminocyclopentenols: total synthesis of carbocyclic (+)-uracil polyoxin C and its alpha-epimer.

Authors:  Fangzheng Li; John B Brogan; Jennifer L Gage; Deyi Zhang; Marvin J Miller
Journal:  J Org Chem       Date:  2004-06-25       Impact factor: 4.354

9.  concise synthesis of 4-acylamino analogues of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acids (LY354740) from an acylnitroso Diels-Alder cycloadduct.

Authors:  Wenlin Lee; Marvin J Miller
Journal:  J Org Chem       Date:  2004-06-25       Impact factor: 4.354

10.  Enantioselective total synthesis of (+)-azimine and (+)-carpaine.

Authors:  Taro Sato; Sakae Aoyagi; Chihiro Kibayashi
Journal:  Org Lett       Date:  2003-10-16       Impact factor: 6.005
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