title: Synthesis of (±)-tetrapetalone A-Me aglycon.
abstract: The first synthesis of (±)-tetrapetalone A-Me aglycon is described. Key bond-forming reactions include Nazarov cyclization, a ring-closing metathesis promoted with complete diastereoselectivity by a chiral molybdenum-based complex, tandem conjugate reduction/intramolecular aldol cyclization, and oxidative dearomatization.
authors.affiliation: Department of Chemistry, University of Rochester, Rochester, NY 14627 (USA).
authors.forename: Peter N
authors.initials: PN
authors.lastname: Carlsen
authors.forename: Tyler J
authors.initials: TJ
authors.lastname: Mann
authors.forename: Amir H
authors.initials: AH
authors.lastname: Hoveyda
authors.forename: Alison J
authors.initials: AJ
authors.lastname: Frontier
mesh_terms: D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D008982:Molybdenum / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; D009942:Organometallic Compounds; C492598:tetrapetalone A; D008982:Molybdenum
keywords: cross-coupling; cyclization; metathesis; natural products; polycycles