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First Enantioselective Total Synthesis of (−)-Centrolobine

2002; American Chemical Society; Volume: 4; Issue: 10 Linguagem: Inglês

10.1021/ol025778z

1523-7060

Françoise Colobert, Renaud Des Mazery, Guy Solladié, M. Carmen Carreño,

Asymmetric Synthesis and Catalysis

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 β-ketosulfoxide 4 is the source of chirality. Revision of the absolute configuration of (−)-Centrolobine is proposed.