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Issue 40, 2017
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Exploration of a Au(I)-mediated three-component reaction for the synthesis of DNA-tagged highly substituted spiroheterocycles

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Abstract

We demonstrate a Au(I)-mediated three-component reaction to DNA-tagged highly substituted 6-oxa-1,2-diazaspiro[4.4]nonanes from either DNA-coupled aldehydes, hydrazides, or alkynols. The choice of the starting material coupled to the DNA tag was critial for the purity of the product as the DNA-aldehyde conjugate yielded the purest products, whereas the alkynol- and hydrazide conjugates returned complex product mixtures. The reaction was compatible with thymine-, cytosine-, and, surprisingly, with adenine-DNA, while guanine-containing DNA strands were degraded under the reaction conditions.

Graphical abstract: Exploration of a Au(i)-mediated three-component reaction for the synthesis of DNA-tagged highly substituted spiroheterocycles

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Publication details

The article was received on 20 Sep 2017, accepted on 27 Sep 2017 and first published on 27 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02347B
Citation: Org. Biomol. Chem., 2017,15, 8648-8654
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    Exploration of a Au(I)-mediated three-component reaction for the synthesis of DNA-tagged highly substituted spiroheterocycles

    M. Klika Škopić, S. Willems, B. Wagner, J. Schieven, N. Krause and A. Brunschweiger, Org. Biomol. Chem., 2017, 15, 8648
    DOI: 10.1039/C7OB02347B

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