title: Function-oriented synthesis: studies aimed at the synthesis and mode of action of 1alpha-alkyldaphnane analogues.
abstract: [reaction: see text] An efficient synthetic route to the ABC tricyclic core of 1alpha-alkyldaphnanes has been developed. The conformational bias imparted by the C6-C9 oxo-bridge of BC-ring system 12 was used to elaborate the ABC-ring system precursor including the introduction of the beta-C5 hydroxyl group. A completely diastereoselective palladium-catalyzed enyne cyclization was then employed to establish the A-ring with a C1 appendage.
authors.affiliation: Department of Chemistry and Department of Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu
authors.forename: Paul A
authors.initials: PA
authors.lastname: Wender
authors.forename: Noel
authors.initials: N
authors.lastname: D'Angelo
authors.forename: Vassil I
authors.initials: VI
authors.lastname: Elitzin
authors.forename: Martin
authors.initials: M
authors.lastname: Ernst
authors.forename: Eileen E
authors.initials: EE
authors.lastname: Jackson-Ugueto
authors.forename: John A
authors.initials: JA
authors.lastname: Kowalski
authors.forename: Sharon
authors.initials: S
authors.lastname: McKendry
authors.forename: Markus
authors.initials: M
authors.lastname: Rehfeuter
authors.forename: Robert
authors.initials: R
authors.lastname: Sun
authors.forename: David
authors.initials: D
authors.lastname: Voigtlaender
mesh_terms: D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D004224:Diterpenes; C011309:mezerein