Literature DB >> 25400299

A New Method for the Cleavage of Nitrobenzyl Amides and Ethers.

Seo-Jung Han1, Gabriel Fernando de Melo1, Brian M Stoltz1.   

Abstract

A mild and efficient o- and p-nitrobenzyl cleavage protocol was developed. o- and p-Nitrobenzyl groups were easily removed from a variety of substrates using 20% aqueous NaOH in methanol at 75 °C, presumably via oxidation at the benzylic position by oxygen dissolved in the solution. These easily introducible and removable nitrobenzyl groups can serve as valuable protecting groups for the synthesis of multifunctional, complex molecules.

Entities:  

Keywords:  Amide protection; Deprotection; Protecting group; o-Nitrobenzyl group; p-Nitrobenzyl group

Year:  2014        PMID： 25400299      PMCID： PMC4228375          DOI： 10.1016/j.tetlet.2014.10.006

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  6 in total

1.  Total Synthesis of (-)-Spirotryprostatin B and Three Stereoisomers We thank NIH NIGMS (GM-30859) for financial support, Prof. A. J. Shaka and N. D. Taylor for DPFGSE experiments, Prof. H. Osada for providing spectral data for natural 1, and Prof. R. M. Williams and P. R. Sebahar for providing spectral data and a sample of synthetic ent-21. We are also grateful to Prof. R. M. Williams and Prof. S. J. Danishefsky for open exchange of information prior to publication. NMR and mass spectra were determined at UC Irvine with instruments purchased with the assistance of the NSF and NIH shared instrumentation programs.

Authors:  Larry E. Overman; Mark D. Rosen
Journal:  Angew Chem Int Ed Engl       Date:  2000-12-15       Impact factor: 15.336

2.  Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine.

Authors:  Andrew Madin; Christopher J O'Donnell; Taeboem Oh; David W Old; Larry E Overman; Matthew J Sharp
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

3.  Synthesis of spirocyclic carbazole- and acridine-lactams.

Authors:  Martina Würdemann; Jens Christoffers
Journal:  Org Biomol Chem       Date:  2010-04-21       Impact factor: 3.876

4.  Synthesis of 4,5-dianilinophthalimide and related analogues for potential treatment of Alzheimer's disease via palladium-catalyzed amination.

Authors:  Edward J Hennessy; Stephen L Buchwald
Journal:  J Org Chem       Date:  2005-09-02       Impact factor: 4.354

5.  From imide to lactam metallo-pyridocarbazoles: distinct scaffolds for the design of selective protein kinase inhibitors.

Authors:  Nicholas Pagano; Eric Y Wong; Tom Breiding; Haidong Liu; Alexander Wilbuer; Howard Bregman; Qi Shen; Scott L Diamond; Eric Meggers
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

6.  A diastereodivergent synthetic strategy for the syntheses of communesin F and perophoramidine.

Authors:  Seo-Jung Han; Florian Vogt; Shyam Krishnan; Jeremy A May; Michele Gatti; Scott C Virgil; Brian M Stoltz
Journal:  Org Lett       Date:  2014-06-09       Impact factor: 6.005
  6 in total
  1 in total

1.  Evolution of a unified, stereodivergent approach to the synthesis of communesin F and perophoramidine.

Authors:  Seo-Jung Han; Florian Vogt; Jeremy A May; Shyam Krishnan; Michele Gatti; Scott C Virgil; Brian M Stoltz
Journal:  J Org Chem       Date:  2014-11-26       Impact factor: 4.354
  1 in total

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