Issue 28, 2012
From the journal:

Chemical Communications

Enantioselective synthesis of (−)-paeonilide†

Klaus Harrara  and  Oliver Reiser*a  

* Corresponding authors

a Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany
E-mail: oliver.reiser@chemie.uni-regensburg.de
Fax: +49 941 943 4121
Tel: +49 941 943 4631

Abstract

The first enantioselective synthesis of (−)-paeonilide is reported. Starting from inexpensive furan-3-carboxylic acid the targeted monoterpene was obtained in 12 steps via an asymmetric cyclopropanation-lactonization cascade and a stereoselective side chain insertion at an acetal-like position.

Graphical abstract: Enantioselective synthesis of (−)-paeonilide

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Article information

DOI
https://doi.org/10.1039/C2CC18172J
Article type
Communication
Submitted
30 Dec 2011
Accepted
09 Feb 2012
First published
23 Feb 2012

Chem. Commun., 2012,48, 3457-3459

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Enantioselective synthesis of (−)-paeonilide

K. Harrar and O. Reiser, Chem. Commun., 2012, 48, 3457 DOI: 10.1039/C2CC18172J

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