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Synthesis 2010(1): 171-179  
DOI: 10.1055/s-0029-1217043
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Racemic and Enantiomerically Pure Acetylenic ω-Keto Esters Derived from 2-Methyl-1,3-cycloalkanediones and 2-Methylcycloalkanones Respectively

Philippe Geoffroya, Marie-Paule Balleta, Sidonie Fincka,1, Eric Marchionib, Christophe Marcicb, Michel Miesch*a
a Université de Strasbourg, Institut de Chimie, UMR 7177, Laboratoire de Chimie Organique Synthétique, 1 rue Blaise Pascal, BP296/R8, 67008 Strasbourg, France
Fax: +33(3)90241754; e-Mail: m.miesch@chimie.u-strasbg.fr;
b Université de Strasbourg, Faculté de Pharmacie, IPCH, UMR 7178, Laboratoire de Chimie Analytique et Sciences de l’Aliment-74, route du Rhin, 67400 Illkirch, France
Further Information

Publication History

Received 6 July 2009
Publication Date:
03 November 2009 (online)

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Abstract

Racemic and enantiomerically pure alkynyl esters tethered, respectively, to 2-methyl-1,3-cycloalkanediones and 2-methyl­cycloalkanones were readily obtained starting from common intermediates, which were available on large scale.

Key words

alkynyl ester - enantiomer-chain - elongation - trimethylsilylpropyne - Corey-Fuchs reaction

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1

In part. S.F. achieved the synthesis of compound 17 by using the synthetic route described in Scheme 4.