Issue 3, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
29 Sep 2016
Accepted
18 Oct 2016
First published
18 Oct 2016

Org. Biomol. Chem., 2017,15, 584-588

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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