Enantioselective total syntheses of the Ipecacuanha alkaloid emetine, the Alangium alkaloid tubulosine and a novel benzoquinolizidine alkaloid by using a domino …

LF Tietze, N Rackelmann…

Index: Tietze, Lutz F.; Rackelmann, Nils; Mueller Chemistry - A European Journal, 2004 , vol. 10, # 11 p. 2722 - 2731

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Citation Number: 106

Abstract

Abstract The first enantioselective syntheses of the Ipecacuanha alkaloid emetine (1) and the Alangium alkaloid tubulosine (2) is described employing a domino Knoevenagel/hetero- Diels–Alder reaction and an enantioselective catalytic transfer hydrogenation of imines as key steps. Thus, hydrogenation of the imine 15 with the catalyst (R, R)-16 gives the tetrahydroisoquinoline 14 with 95% ee which was transformed into the aldehyde (1S)-7. ...