Total Synthesis of (−)-Galanthamine and (−)-Lycoramine via Catalytic Asymmetric Hydrogenation and Intramolecular Reductive Heck Cyclization

Total Synthesis of (−)-Galanthamine and (−)-Lycoramine via Catalytic Asymmetric Hydrogenation and Intramolecular Reductive Heck Cyclization

A synthetic strategy featuring efficient ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryloxy cyclic ketone via dynamic kinetic resolution and palladium-catalyzed intramolecular reductive Heck cyclization has been developed for the asymmetric total synthesis of (−)-galanthamine (20.1%,...

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Veröffentlicht in:Organic letters 2012-06, Vol.14 (11), p.2714-2717
Hauptverfasser: Chen, Ji-Qiang, Xie, Jian-Hua, Bao, Deng-Hui, Liu, Sheng, Zhou, Qi-Lin
Format: Artikel
Sprache:eng
Schlagworte:
Amaryllidaceae Alkaloids - chemical synthesis
Amaryllidaceae Alkaloids - chemistry
Catalysis
Cyclization
Galantamine - chemical synthesis
Galantamine - chemistry
Hydrogenation
Molecular Structure
Palladium - chemistry
Ruthenium - chemistry
Stereoisomerism
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Zusammenfassung:A synthetic strategy featuring efficient ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryloxy cyclic ketone via dynamic kinetic resolution and palladium-catalyzed intramolecular reductive Heck cyclization has been developed for the asymmetric total synthesis of (−)-galanthamine (20.1%, 12 steps) and (−)-lycoramine (40.2%, 10 steps)
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300913g