Related Experiment Videos
First enantioselective total synthesis of (-)-Centrolobine
Françoise Colobert1, Renaud Des Mazery, Guy Solladié
1Laboratoire 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
Organic Letters
|May 10, 2002
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.