title: A practical deca-gram scale ring expansion of (R)-(-)-carvone to (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1.
abstract: A route to enantiopure (R)-(+)-3-methyl-6-isopropenyl-cyclohept-3-enone-1, an intermediate for terpenoids, has been developed and includes a highly chemo- and regioselective Tiffeneau-Demjanov reaction. Starting from readily available (R)-(-)-carvone, this robust sequence is available on a deca-gram scale and uses flow chemistry for the initial epoxidation reaction. The stereochemistry of the addition of two nucleophiles to the carbonyl group of (R)-(-)-carvone has been determined by X-ray diffraction studies and chemical correlation.
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos, P.O. Box 676, 13565-905, São Carlos - SP, Brazil. brocksom@terra.com.br.
authors.forename: Leandro de C
authors.initials: Lde C
authors.lastname: Alves
authors.forename: André L
authors.initials: AL
authors.lastname: Desiderá
authors.forename: Kleber T
authors.initials: KT
authors.lastname: de Oliveira
authors.forename: Sean
authors.initials: S
authors.lastname: Newton
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Brocksom
mesh_terms: D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D000081005:Cyclohexane Monoterpenes; D008968:Molecular Conformation; D039821:Monoterpenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003508:Cycloheptanes; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; C006923:carvone