title: Rapid construction of the ABC ring system in the Daphniphyllum alkaloid daphniyunnine C.
abstract: An efficient and scalable synthesis of the ABC ring system common to the calyciphylline A-type alkaloids has been developed. The tricyclic core of the alkaloids features a bowl-shaped [6-6-5] skeleton with five stereogenic centers including an all-carbon quaternary center. It was constructed rapidly from a readily available carvone derivative through a seven-step sequence involving an aza-Michael addition and Pd-catalyzed enolate α-vinylation as key steps.
authors.affiliation: State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin, China, 300071.
authors.forename: Yanmin
authors.initials: Y
authors.lastname: Yao
authors.forename: Guangxin
authors.initials: G
authors.lastname: Liang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D031995:Saxifragaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C578161:daphniyunnine C