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Total Synthesis of (±)-Halomon by a Johnson-Claisen Rearrangement
Thierry Schlama1, Rachid Baati1, Véronique Gouverneur1
1Université 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.
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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