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Issue 19, 2008
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Synthesis of spiroacetal-triazoles as privileged natural product-like scaffolds using “click chemistry”

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Abstract

The elaboration of a 6,6-spiroacetal scaffold to incorporate a triazole unit as a peptide bond surrogate at the anomeric position is described. The novel spiroacetal-triazole hybrid structures were generated viacycloaddition of a spiroacetal azide to a series of alkynes. The spiroacetal framework was constructed viaBarbier reaction of bromide 10 with Weinreb amide 11, followed by acid-catalysed deprotection and cyclisation to afford the 6,6-spiroacetal ring system. The resultant ethoxy-spiroacetal 8 was converted to spiroacetal azide 5, which was then elaborated into a series of spiroacetal-triazole derivatives 7.

Graphical abstract: Synthesis of spiroacetal-triazoles as privileged natural product-like scaffolds using “click chemistry”

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Publication details

The article was received on 19 May 2008, accepted on 09 Jul 2008 and first published on 05 Aug 2008


Article type: Paper
DOI: 10.1039/B808454H
Citation: Org. Biomol. Chem., 2008,6, 3518-3526
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    Synthesis of spiroacetal-triazoles as privileged natural product-like scaffolds using “click chemistry”

    K. W. Choi and M. A. Brimble, Org. Biomol. Chem., 2008, 6, 3518
    DOI: 10.1039/B808454H

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