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Issue 3, 2017
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Acid-catalysed intramolecular addition of β-ketoesters to 1,3-dienes

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Abstract

1,3-Dienyl β-keto esters are cyclised into bicyclolactones using the Bi(OTf)3/TfOH catalytic system. This reaction represents a rare case of simultaneous C–C and C–O bond formation at positions 1 and 3 of a 1,3-diene. Application to the synthesis of ramulosin is presented.

Graphical abstract: Acid-catalysed intramolecular addition of β-ketoesters to 1,3-dienes

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Publication details

The article was received on 29 Sep 2016, accepted on 18 Oct 2016 and first published on 18 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB02122K
Citation: Org. Biomol. Chem., 2017,15, 584-588
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    Acid-catalysed intramolecular addition of β-ketoesters to 1,3-dienes

    M. Vayer, W. Fang, R. Guillot, S. Bezzenine-Lafollée, C. Bour and V. Gandon, Org. Biomol. Chem., 2017, 15, 584
    DOI: 10.1039/C6OB02122K

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