title: Rapid access to the heterocyclic core of the calyciphylline A and daphnicyclidin A-type Daphniphyllum alkaloids via tandem cyclization of a neutral aminyl radical.
abstract: A streamlined approach to the tertiary amine-containing core of the calyciphylline A and daphnicyclidin A-type Daphniphyllum alkaloids is presented. A known carvone derivative is converted into the core structure in only four synthetic operations, and it is well poised for further elaboration. The key enabling methodology is a radical cyclization cascade beginning with addition of a secondary, neutral aminyl radical to the β-position of an enone, followed by trapping with a pendant alkyne.
authors: Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States.
authors: Ahmad A
authors: AA
authors: Ibrahim
authors: Alexander N
authors: AN
authors: Golonka
authors: Alberto M
authors: AM
authors: Lopez
authors: Jennifer L
authors: JL
authors: Stockdill
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D003500:Cyclization; D000081005:Cyclohexane Monoterpenes; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D031995:Saxifragaceae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000588:Amines; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D011083:Polycyclic Compounds; C479143:calyciphylline A; C540244:daphnicyclidin A; C006923:carvone