A new synthesis of (+)- and (-)-cherylline.
A new and concise synthesis of enantiopure antipodes of alkaloid cherylline has been devised. The synthetic strategy relies upon the reduction of a diversely and polyprotected diarylenamine bearing a chiral auxiliary. Separation of diastereopure intermediates, concomitant deprotections and intramolecular reductive amination complete the synthesis of the natural (S)-enantiomer and of the unnatural (R)-configured antipode.
Lebrun
Stéphane
S
Laboratoire de Chimie Organique Physique, associé à l'ENSCL, UMR 8009, Université des Sciences et Technologies de Lille 1, F-59655 Villeneuve d'Ascq, France.
Couture
Axel
A
Deniau
Eric
E
Grandclaudon
Pierre
P
D000470:Alkaloids / Q000138:chemical synthesis; D047151:Amaryllidaceae Alkaloids; D000586:Amination; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D007546:Isoquinolines; C424145:cherylline