title: A new synthesis of (+)- and (-)-cherylline.
abstract: 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.
authors.affiliation: 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.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Lebrun
authors.forename: Axel
authors.initials: A
authors.lastname: Couture
authors.forename: Eric
authors.initials: E
authors.lastname: Deniau
authors.forename: Pierre
authors.initials: P
authors.lastname: Grandclaudon
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis; D047151:Amaryllidaceae Alkaloids; D000586:Amination; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D007546:Isoquinolines; C424145:cherylline