title: Synthesis of complex hexacyclic compounds via a tandem Rh(II)-catalyzed double-cyclopropanation/Cope rearrangement/Diels-Alder reaction.
abstract: Treatment of (E)-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene with styryl diazoacetates in the presence of catalytic amounts of the dirhodium complex Rh2(S-DOSP)4 provides a highly enantioenriched hexacyclic product with 10 new stereogenic centers. The transformation proceeds by a cascade sequence starting with a double cyclopropanation of a benzene ring, followed by a Cope rearrangement of a divinylcyclopropane and then an intramolecular Diels-Alder cycloaddition.
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Jillian E
authors.initials: JE
authors.lastname: Spangler
authors.forename: Yajing
authors.initials: Y
authors.lastname: Lian
authors.forename: Sandeep N
authors.initials: SN
authors.lastname: Raikar
authors.forename: Huw M L
authors.initials: HM
authors.lastname: Davies
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D003979:Diazonium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000737:chemistry*
chemical_list: C000599277:(E)-1-(methoxymethylene)-1,2,3,4-tetrahydronaphthalene; D003979:Diazonium Compounds; D009942:Organometallic Compounds; D013764:Tetrahydronaphthalenes; C407352:dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); D011392:Proline; D012238:Rhodium