title: Expedient construction of the [7-5-5] all-carbon tricyclic core of the Daphniphyllum alkaloids daphnilongeranin B and daphniyunnine D.
abstract: A synthetic strategy for the construction of the [7-5-5] all-carbon tricyclic core of numerous calyciphylline A-type Daphniphyllum alkaloids has been developed using a key intramolecular Pauson-Khand reaction. A subsequent base-mediated double-bond migration and a regio- and stereoselective radical late stage allylic oxygenation provide access to the substitution patterns of daphnilongeranin B and daphniyunnine D.
authors.affiliation: Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
authors.forename: Benjamin
authors.initials: B
authors.lastname: Darses
authors.forename: Iacovos N
authors.initials: IN
authors.lastname: Michaelides
authors.forename: Filippo
authors.initials: F
authors.lastname: Sladojevich
authors.forename: John W
authors.initials: JW
authors.lastname: Ward
authors.forename: Paula R
authors.initials: PR
authors.lastname: Rzepa
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D031995:Saxifragaceae / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C558838:daphnilongeranin B; C572469:daphniyunnine D