Literature DB >> 21709827

A Mild, Large-Scale Synthesis of 1,3-Cyclooctanedione: Expanding Access to Difluorinated Cyclooctyne for Copper-Free Click Chemistry.

Evan A Sims1, Cole A Deforest, Kristi S Anseth.   

Abstract

We report the large-scale synthesis of 1,3-cyclooctanedione in five steps with 29% yield. This molecule is a synthetic precurser to difluorinated cyclooctyne, which participates in a bioorthogonal copper-free click reaction with azides. The final step demonstrates the first successful application of the Wacker-Tsuji oxidation to form a cyclic 1,3-dione.

Entities:  

Year:  2011        PMID： 21709827      PMCID： PMC3103834          DOI： 10.1016/j.tetlet.2011.02.029

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


  16 in total

1.  Stereocontrolled construction of an ingenol prototype having a complete array of oxygenated and unsaturated centers.

Authors:  L A Paquette; R J Ross; J P Springer
Journal:  J Am Chem Soc       Date:  1988-08-01       Impact factor: 15.419

2.  Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions.

Authors:  Xinghai Ning; Jun Guo; Margreet A Wolfert; Geert-Jan Boons
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition.

Authors:  Marjoke F Debets; Sander S van Berkel; Sanne Schoffelen; Floris P J T Rutjes; Jan C M van Hest; Floris L van Delft
Journal:  Chem Commun (Camb)       Date:  2009-11-06       Impact factor: 6.222

4.  Viability study of HL60 cells in contact with commonly used microchip materials.

Authors:  Floor Wolbers; Paul ter Braak; Severine Le Gac; Regina Luttge; Helene Andersson; Istvan Vermes; Albert van den Berg
Journal:  Electrophoresis       Date:  2006-12       Impact factor: 3.535

5.  Peptide-Functionalized Click Hydrogels with Independently Tunable Mechanics and Chemical Functionality for 3D Cell Culture.

Authors:  Cole A Deforest; Evan A Sims; Kristi S Anseth
Journal:  Chem Mater       Date:  2010-07-22       Impact factor: 9.811

6.  Copper-free click chemistry for the in situ crosslinking of photodegradable star polymers.

Authors:  Jeremiah A Johnson; Jeremy M Baskin; Carolyn R Bertozzi; Jeffrey T Koberstein; Nicholas J Turro
Journal:  Chem Commun (Camb)       Date:  2008-04-24       Impact factor: 6.222

7.  Second-generation difluorinated cyclooctynes for copper-free click chemistry.

Authors:  Julian A Codelli; Jeremy M Baskin; Nicholas J Agard; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2008-08-05       Impact factor: 15.419

8.  Sequential click reactions for synthesizing and patterning three-dimensional cell microenvironments.

Authors:  Cole A DeForest; Brian D Polizzotti; Kristi S Anseth
Journal:  Nat Mater       Date:  2009-06-21       Impact factor: 43.841

9.  Bioorthogonal chemistry: fishing for selectivity in a sea of functionality.

Authors:  Ellen M Sletten; Carolyn R Bertozzi
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  In vivo imaging of membrane-associated glycans in developing zebrafish.

Authors:  Scott T Laughlin; Jeremy M Baskin; Sharon L Amacher; Carolyn R Bertozzi
Journal:  Science       Date:  2008-05-02       Impact factor: 47.728
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  5 in total

1.  A photoreversible protein-patterning approach for guiding stem cell fate in three-dimensional gels.

Authors:  Cole A DeForest; David A Tirrell
Journal:  Nat Mater       Date:  2015-02-23       Impact factor: 43.841

2.  Photoreversible patterning of biomolecules within click-based hydrogels.

Authors:  Cole A DeForest; Kristi S Anseth
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-08       Impact factor: 15.336

3.  Cytocompatible click-based hydrogels with dynamically tunable properties through orthogonal photoconjugation and photocleavage reactions.

Authors:  Cole A DeForest; Kristi S Anseth
Journal:  Nat Chem       Date:  2011-10-23       Impact factor: 24.427

4.  Synthetically tractable click hydrogels for three-dimensional cell culture formed using tetrazine-norbornene chemistry.

Authors:  Daniel L Alge; Malar A Azagarsamy; Dillon F Donohue; Kristi S Anseth
Journal:  Biomacromolecules       Date:  2013-03-08       Impact factor: 6.988

5.  A homologation approach to the synthesis of difluorinated cycloalkynes.

Authors:  Ellen M Sletten; Gabriela de Almeida; Carolyn R Bertozzi
Journal:  Org Lett       Date:  2014-03-03       Impact factor: 6.005
  5 in total

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