Enantioselective synthesis of (+)‐(S)‐laudanosine and (-)‐(S)‐xylopinine

• Verfasst von: Mujahidin, Didin [VerfasserIn]
• Verfasst von: Doye, Sven [VerfasserIn]
• Titel: Enantioselective synthesis of (+)‐(S)‐laudanosine and (-)‐(S)‐xylopinine
• Verf.angabe: Didin Mujahidin and Sven Doye
• Umfang: 5 S.
• Fussnoten: Gesehen am 21.03.2018
• Titel Quelle: Enthalten in: European journal of organic chemistry
• Jahr Quelle: 2005
• Band/Heft Quelle: (2005), 13, S. 2689-2693
• ISSN Quelle: 1099-0690
• DOI: doi:10.1002/ejoc.200500095
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1571310304

Abstract

Abstract: The study presents a new pathway for the enantioselective synthesis of benzylisoquinoline alkaloids. The key steps of the synthesis of (+)-(S)-laudanosine (1) and (-)-(S)-xylopinine (2) are a Sonogashira coupling that builds up the C1-C8a bond of the benzylisoquinoline skeleton, an intramolecular Ti-catalyzed hydroamination of an alkyne, and a subsequent enantioselective imine reduction according to Noyori's protocol.