title: Stereocontrolled syntheses of tetralone- and naphthyl-type lignans by a one-pot oxidative [3,3] rearrangement/Friedel-Crafts arylation.
abstract: The development of a stereoselective one-pot oxidative [3,3] sigmatropic rearrangement/Friedel-Crafts arylation that provides enantioenriched benzhydryl compounds is reported. The utility of this new transformation is demonstrated by the concise synthesis of several tetralone- and naphthyl-type lignan natural products, many of which display anti-malarial activity.
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Rd, Evanston, IL 60208 (USA).
authors.forename: Jordan C T
authors.initials: JC
authors.lastname: Reddel
authors.forename: Kelly E
authors.initials: KE
authors.lastname: Lutz
authors.forename: Abdallah B
authors.initials: AB
authors.lastname: Diagne
authors.forename: Regan J
authors.initials: RJ
authors.lastname: Thomson
mesh_terms: D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D044024:Tetralones / Q000737:chemistry*
chemical_list: D000962:Antimalarials; D006835:Hydrazones; D017705:Lignans; D044024:Tetralones; C568373:pycnanthulignene B
keywords: cascade reactions; hydrazones; lignans; natural product synthesis; sigmatropic rearrangement