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Issue 30, 2012
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Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds

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Abstract

The enantioselective synthesis of novel C-linked spiroacetal-triazoles 10 is reported. The key step involves reaction of acetylenic spiroacetal 11 with several azides by the Copper-Catalysed AzideAlkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold 11 was prepared from silyl-protected Weinreb amide 19 using several reliable Grignard additions and a highly diastereoselective enzymatic kinetic resolution.

Graphical abstract: Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds

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Publication details

The article was received on 27 Oct 2011, accepted on 30 Nov 2011 and first published on 01 Dec 2011


Article type: Paper
DOI: 10.1039/C2OB06802H
Org. Biomol. Chem., 2012,10, 5993-6002

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    Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds

    J. T. B. Kueh, K. W. Choi and M. A. Brimble, Org. Biomol. Chem., 2012, 10, 5993
    DOI: 10.1039/C2OB06802H

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