Literature DB >> 18007438

A novel strategy towards the asymmetric synthesis of orthogonally funtionalised 2-N-benzyl-N-alpha-methylbenzylamino- 5-carboxymethyl-cyclopentane-1-carboxylic acid.

Narciso M Garrido1, Mohamed M El Hammoumi, David Díez, Mercedes García, Julio G Urones.   

Abstract

The asymmetric synthesis of the orthogonally funtionalised compounds tert-butyl 2-N-benzyl-N-alpha-methylbenzylamino-5-methoxycarbonylmethylcyclopentane- 1-carboxylate and methyl 2-N-benzyl-N-alpha-methylbenzylamino-5-carboxymethylcyclo- pentane-1-carboxylate by a domino reaction of tert-butyl methyl (E,E)-octa-2,6- diendioate with lithium N-alpha-methylbenzyl-N-benzylamide initiated by a Michael addition, subsequent 5-exo-trig intramolecular cyclisation and posterior selective hydrolysis with trifluoroacetic acid is reported.

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Year:  2004        PMID： 18007438      PMCID： PMC6147460          DOI： 10.3390/90500373

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  7 in total

1.  Non-haemolytic beta-amino-acid oligomers.

Authors:  E A Porter; X Wang; H S Lee; B Weisblum; S H Gellman
Journal:  Nature       Date:  2000-04-06       Impact factor: 49.962

Review 2.  beta-Peptides: from structure to function.

Authors:  R P Cheng; S H Gellman; W F DeGrado
Journal:  Chem Rev       Date:  2001-10       Impact factor: 60.622

3.  cis-2-aminocyclopentanecarboxylic acid oligomers adopt a sheetlike structure: switch from helix to nonpolar strand.

Authors:  Tamás A Martinek; Gábor K Tóth; Elemer Vass; Miklós Hollósi; Ferenc Fülöp
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

4.  Residue-based control of helix shape in beta-peptide oligomers.

Authors:  D H Appella; L A Christianson; D A Klein; D R Powell; X Huang; J J Barchi; S H Gellman
Journal:  Nature       Date:  1997-05-22       Impact factor: 49.962

5.  Stereoselective synthesis of 3-substituted 2-aminocyclopentanecarboxylic acid derivatives and their incorporation into short 12-helical beta-peptides that fold in water.

Authors:  Matthew G Woll; John D Fisk; Paul R LePlae; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2002-10-23       Impact factor: 15.419

6.  Synthesis and 12-helical secondary structure of beta-peptides containing (2R,3R)-aminoproline.

Authors:  Emilie A Porter; Xifang Wang; Margaret A Schmitt; Samuel H Gellman
Journal:  Org Lett       Date:  2002-09-19       Impact factor: 6.005

7.  Asymmetric synthesis of the stereoisomers of 2-amino-5-carboxymethyl-cyclopentane-1-carboxylate.

Authors:  Julio G Urones; Narciso M Garrido; David Díez; Mohamed M El Hammoumi; Sara H Dominguez; J Antonio Casaseca; Stephen G Davies; Andrew D Smith
Journal:  Org Biomol Chem       Date:  2004-01-05       Impact factor: 3.876
  7 in total
  2 in total

1.  Synthesis and Modeling of Ezetimibe Analogues.

Authors:  Mateo M Salgado; Alejandro Manchado; Carlos T Nieto; David Díez; Narciso M Garrido
Journal:  Molecules       Date:  2021-05-22       Impact factor: 4.411

2.  Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products.

Authors:  Alejandro Manchado; Victoria Elena Ramos; David Díez; Narciso M Garrido
Journal:  Molecules       Date:  2020-03-13       Impact factor: 4.411
  2 in total

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