Synthesis 2010(7): 1223-1228  
DOI: 10.1055/s-0029-1218604
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (1-Allylcyclohexa-2,5-dienyl)arenes

Géraldine Rousseau, Frédéric Robert, Yannick Landais*
Université de Bordeaux, UMR-CNRS 5255, 351, cours de la libération, 33405 Talence Cedex, France
Fax: +33(5)40006286; e-Mail: y.landais@ism.u-bordeaux1.fr;
Further Information

Publication History

Received 20 October 2009
Publication Date:
11 December 2009 (eFirst)

Abstract

(1-Allylcyclohexa-2,5-dienyl)arenes are useful building blocks for the synthesis of natural products including amaryllidaceae, strychnos and morphinan alkaloids. Their synthesis was carried out in a straightforward manner starting from readily available cyclohexane-1,3-dione, through a palladium-mediated arylation-allylation sequence, which was used to install the quaternary center, followed by a transformation of the resulting 1,3-dione into the required diene through generation of a bis-silyl enol ether. After conversion of the latter into the corresponding bis-enol triflate, it was finally hydrogenated using palladium catalysis to give the title compounds.

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