Diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry

Zaware, N and LaPorte, MG and Farid, R and Liu, L and Wipf, P and Floreancig, PE (2011) Diversity-oriented synthesis of a library of substituted tetrahydropyrones using oxidative carbon-hydrogen bond activation and click chemistry. Molecules, 16 (5). 3648 - 3662.

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Abstract

Eighteen (2RS,6RS)-2-(4-methoxyphenyl)-6-(substituted ethyl)dihydro- 2Hpyran-4(3H)ones were synthesized via a DDQ-mediated oxidative carbon-hydrogen bond activation reaction. Fourteen of these tetrahydropyrans were substituted with triazoles readily assembled via azide-alkyne click-chemistry reactions. Examples of a linked benzotriazole and pyrazole motif were also prepared. To complement the structural diversity, the alcohol substrates were obtained from stereoselective reductions of the tetrahydropyrone. This library provides rapid access to structurally diverse non-natural compounds to be screened against a variety of biological targets. © 2011 by the authors.

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Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Zaware, N LaPorte, MG Farid, R Liu, L Wipf, P pwipf@pitt.edu PWIPF Floreancig, PE
Date:	1 May 2011
Date Type:	Publication
Journal or Publication Title:	Molecules
Volume:	16
Number:	5
Page Range:	3648 - 3662
DOI or Unique Handle:	10.3390/molecules16053648
Schools and Programs:	Dietrich School of Arts and Sciences > Chemistry
Refereed:	Yes
MeSH Headings:	Click Chemistry--methods; Magnetic Resonance Spectroscopy; Molecular Structure; Oxidation-Reduction; Pyrans--chemical synthesis; Pyrans--chemistry
PubMed ID:	21540794
Date Deposited:	31 Jul 2014 20:49
Last Modified:	03 Feb 2019 06:55
URI:	http://d-scholarship.pitt.edu/id/eprint/22336

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