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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, Email: frederic.lecornueuniv-poitiers.fr

J. Tallineau, G. Bashiardes, J.-M. Coustard, F. Lecornué, Synlett, 2009, 2761-2764.

DOI: 10.1055/s-0029-1217964 (free Supporting Information)


Abstract

The reaction of organocerium reagents, generated in situ from aryl and heteroaryl lithium compounds, with cycloalkanones proceeds cleanly to provide alkoxides. Addition of MsCl or SOCl2 with DBU gave aryl-substituted cycloalkenes in good yields. A short total synthesis of (±)-laurokamurene B is described.

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Laurokamurene B



Key Words

organocerium reagents, addition reactions, eliminations, cycloalkenes, cyclopentenes, cyclohexenes, cycloheptenes, olefination of arenes, laurokamurene B


ID: J60-Y2009-2830