First enantioselective total synthesis of (-)-Centrolobine |
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| Authors: | Colobert Françoise Mazery Renaud Des Solladié Guy Carreño M Carmen |
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| Institution: | Laboratoire de Stéréochimie associé au CNRS, Université Louis Pasteur, E.C.P.M., 25 rue Becquerel 67087 Strasbourg Cedex 2, France. fcolober@chimie.u-strasbg.fr |
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| Abstract: | structure: see text] The first enantioselective total synthesis of (-)-Centrolobine is described. The key reaction is the synthesis of the cis-disubstituted tetrahydropyran framework by intramolecular cyclization of the enantiopure hydroxyketone 3 with Et3SiH and TMSOTf. The stereoselective reduction of the beta-ketosulfoxide 4 is the source of chirality. Revision of the absolute configuration of (-)-Centrolobine is proposed. |
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