Total Synthesis of (±)-Halomon by a Johnson–Claisen Rearrangement

Authors

  • Thierry Schlama,

    1. Université Louis Pasteur, Faculté de Pharmacie, Laboratoire de Synthèse Bioorganique associé au CNRS, 74, route du Rhin, BP-24, 67401 Illkirch (France), Fax: (+33) 3-88-67-88-91
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  • Rachid Baati,

    1. Université Louis Pasteur, Faculté de Pharmacie, Laboratoire de Synthèse Bioorganique associé au CNRS, 74, route du Rhin, BP-24, 67401 Illkirch (France), Fax: (+33) 3-88-67-88-91
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  • Véronique Gouverneur,

    1. Université Louis Pasteur, Faculté de Pharmacie, Laboratoire de Synthèse Bioorganique associé au CNRS, 74, route du Rhin, BP-24, 67401 Illkirch (France), Fax: (+33) 3-88-67-88-91
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  • Alain Valleix,

    1. CEA Saclay, Service des Molécules Marquées, Bat. 547, Département de Biologie Cellulaire et Moléculaire, F-91191 Gif-sur-Yvette (France)
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  • John R. Falck,

    1. Department of Biochemistry, Southwestern Medical Center, University of Texas, 5323 Harry Hines Blvd., Dallas, TX 75235–9038 (USA)
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  • Charles Mioskowski

    1. Université Louis Pasteur, Faculté de Pharmacie, Laboratoire de Synthèse Bioorganique associé au CNRS, 74, route du Rhin, BP-24, 67401 Illkirch (France), Fax: (+33) 3-88-67-88-91
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Abstract

The total synthesis of the polyhalogenated antitumour agent halomon (1) was accomplished with two novel transformations as key steps: a Johnson–Claisen rearrangement of a dichlorinated alkene for the preparation of the tertiary chlorinated C3 and a new rearrangement of bromohydrins for the regiospecific introduction of the bromine and chlorine atoms on C6 and C7, respectively.

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