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

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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

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Key Words

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

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ID: J60-Y2009-2830