Asymmetric synthesis of (-)-1-hydroxyquinolizidinone, a common intermediate for the syntheses of (-)-homopumiliotoxin 223G and (-)-epiquinamide.
The short and efficient asymmetric synthesis of (-)-1-hydroxyquinolizidinone was achieved in seven steps and 25.2% overall yield from readily available 5-chloropentanal. It is a key intermediate in the formal syntheses of (-)-homopumilotoxin 223G and (-)-epiquinamide.
Voituriez
Arnaud
A
Université Pierre et Marie Curie-Paris 6, Laboratoire de Chimie Organique (UMR CNRS 7611), Institut de Chimie Moléculaire (FR 2769), case 183, 4 place Jussieu, Paris Cedex 05, France.
Ferreira
Franck
F
Pérez-Luna
Alejandro
A
Chemla
Fabrice
F
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry
C524835:1-hydroxyquinolizidinone; D000470:Alkaloids; D007097:Imines; D007212:Indolizines; D010880:Piperidines; D054837:Quinolizidines; D011807:Quinolizines; D013452:Sulfonium Compounds; C481035:epiquinamide; C414694:homopumiliotoxin 223G; C522016:sulfinimine