Literature DB >> 16388662

Regioselective synthesis of alpha-methyl 2-methyleneglutarate via a novel lactonization-elimination rearrangement.

David M Bartley1, James K Coward.   

Abstract

[reaction: see text] A facile route to the alpha-methyl ester of 2-methyleneglutarate via a three-step sequence from 3-hydroxymethylcyclopentene is described. Regioselective formation of the monoacid from a diester precursor proceeds via a novel fluoride-mediated, tandem deprotection/rearrangement of O-silyl 2-(hydroxymethyl)dimethylglutarate.

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Year:  2006        PMID： 16388662      PMCID： PMC2082008          DOI： 10.1021/jo051854a

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


  6 in total

1.  Total Synthesis of Hybocarpone We thank Dr. D. H. Huang, Dr. G. Siuzdak and Dr. I. Ioannou for NMR spectroscopic, mass spectrometric and computational assistance, respectively. Financial support for this work was provided by the Skaggs Institute for Chemical Biology, the National Institutes of Health (USA), and grants from Abbott, Amgen, ArrayBiopharma, Boehringer-Ingelheim, Glaxo, Hoffmann-La Roche, DuPont, Merck, Novartis, Pfizer, CaPCURE, and Schering Plough.

Authors:  K. C. Nicolaou; David Gray
Journal:  Angew Chem Int Ed Engl       Date:  2001-02-16       Impact factor: 15.336

2.  Phosphinic acid pseudopeptides analogous to glutamyl-gamma-glutamate: synthesis and coupling to pteroyl azides leads to potent inhibitors of folylpoly-gamma-glutamate synthetase.

Authors:  N Valiaeva; D Bartley; T Konno; J K Coward
Journal:  J Org Chem       Date:  2001-07-27       Impact factor: 4.354

3.  A stereoselective synthesis of phosphinic acid phosphapeptides corresponding to glutamyl-gamma-glutamate and incorporation into potent inhibitors of folylpoly-gamma-glutamyl synthetase.

Authors:  David M Bartley; James K Coward
Journal:  J Org Chem       Date:  2005-08-19       Impact factor: 4.354

4.  Design and pharmacological activity of phosphinic acid based NAALADase inhibitors.

Authors:  P F Jackson; K L Tays; K M Maclin; Y S Ko; W Li; D Vitharana; T Tsukamoto; D Stoermer; X C Lu; K Wozniak; B S Slusher
Journal:  J Med Chem       Date:  2001-11-22       Impact factor: 7.446

5.  Phosphonate and phosphinate analogues of N-acylated gamma-glutamylglutamate. potent inhibitors of glutamate carboxypeptidase II.

Authors:  Takashi Tsukamoto; Juliet M Flanary; Camilo Rojas; Barbara S Slusher; Nadya Valiaeva; James K Coward
Journal:  Bioorg Med Chem Lett       Date:  2002-08-19       Impact factor: 2.823

6.  Design, synthesis, and biological activity of a potent inhibitor of the neuropeptidase N-acetylated alpha-linked acidic dipeptidase.

Authors:  P F Jackson; D C Cole; B S Slusher; S L Stetz; L E Ross; B A Donzanti; D A Trainor
Journal:  J Med Chem       Date:  1996-01-19       Impact factor: 7.446
  6 in total
  1 in total

1.  Synthesis of isopeptide epoxide peptidomimetics.

Authors:  Debatosh Majumdar; Matthew D Alexander; James K Coward
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354
  1 in total

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