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Synlett 2009(17): 2761-2764  
DOI: 10.1055/s-0029-1217964
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A One-Pot Preparation of Aryl- and Heteroarylcycloalkenes: Application to the Total Synthesis of (±)-Laurokamurene B

Jean Tallineau, Georges Bashiardes, Jean-Marie Coustard, Frédéric Lecornué*
Laboratoire Synthèse et Réactivité des Substances Naturelles, Université de Poitiers, UMR-CNRS 6514, 40 Avenue du Recteur Pineau, 86022 Poitiers Cedex, France
Fax: +33(5)49453965; e-Mail: frederic.lecornue@univ-poitiers.fr;
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Publication History

Received 26 May 2009
Publication Date:
09 September 2009 (online)

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Abstract

A general one-pot method has been developed for the preparation of various aryl- and heteroarylcycloalkenes. After lithiation of aryl and heteroaryl bromides followed by transmetalation with CeCl3, the organocerium addition to cycloalkanones proceeds cleanly to provide the intermediate alkoxide. Addition of MsCl or SOCl2 with DBU gave aryl-substituted cycloalkenes in good yields. A short total synthesis of (±)-laurokamurene B making use of this reaction is described.

Key words

organocerium reagents - addition reactions - eliminations - arylcycloalkenes - laurokamurene B

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18

Srikrishna et al.¹6c did not succeed to purify the ketone 5 and characterized this one as the corresponding tosylhydrazone.