Literature DB >> 19473044

Accessing skeletal diversity using catalyst control: formation of n and n + 1 macrocyclic triazole rings.

Ann Rowley Kelly1, Jingqiang Wei, Sarathy Kesavan, Jean-Charles Marié, Nicole Windmon, Damian W Young, Lisa A Marcaurelle.   

Abstract

A regioselective intramolecular Huisgen cycloaddition was performed on various azido alkyne substrates giving rise to macrocyclic triazole rings. Using catalyst control, a common intermediate has been converted to two structurally unique macrocycles with either a 1,5- or a 1,4-triazole resulting in an n or n + 1 ring size. This is the first example of an intramolecular ruthenium-catalyzed Huisgen cycloaddition.

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Year:  2009        PMID： 19473044      PMCID： PMC2702139          DOI： 10.1021/ol900562u

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  16 in total

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3.  Click chemistry as a macrocyclization tool in the solid-phase synthesis of small cyclic peptides.

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4.  An approach to skeletal diversity using functional group pairing of multifunctional scaffolds.

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5.  Ruthenium-catalyzed cycloaddition of alkynes and organic azides.

Authors:  Li Zhang; Xinguo Chen; Peng Xue; Herman H Y Sun; Ian D Williams; K Barry Sharpless; Valery V Fokin; Guochen Jia
Journal:  J Am Chem Soc       Date:  2005-11-23       Impact factor: 15.419

6.  Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism.

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8.  Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide.

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9.  1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin.

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  11 in total

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3.  Preparation of 1,5-Disubstituted 1,2,3-Triazoles via Ruthenium-catalyzed Azide Alkyne Cycloaddition.

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6.  Regioselective intramolecular dipolar cycloaddition of azides and unsymmetrical alkynes.

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Review 9.  Synthetic and computational efforts towards the development of peptidomimetics and small-molecule SARS-CoV 3CLpro inhibitors.

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10.  Macrocyclic inhibitors of 3C and 3C-like proteases of picornavirus, norovirus, and coronavirus.

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