Sulfoxide‐Directed Stereocontrolled Access to 2H‐Chromans: Total Synthesis of the (S,R,R,R)‐Enantiomer of the Antihypertensive Drug Nebivolol

作者: M. Carmen Carreño , Gloria Hernández-Torres , Antonio Urbano , Françoise Colobert

DOI: 10.1002/EJOC.200800201

关键词: SulfoxideDeoxygenationEnantiomerNebivololStereoselectivityAntihypertensive drugEnantioselective synthesisStereochemistryTotal synthesisOrganic chemistryChemistry

摘要: A homochiral sulfoxide-directed reductive deoxygenation of 2-(p-tolylsulfinyl)methyl-2-chromanols allows the stereoselective formation 2H-chromans with up to 95:5 diastereoisomeric ratio. This new methodology was appliedin a short and convergent enantioselective synthesis ofthe (S,R,R,R)-enantiomer antihypertensive drugNebivolol.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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