title: An enantioselective access to 1-alkyl-1,2,3,4-tetrahydroisoquinolines. Application to a new synthesis of (-)-argemonine.
abstract: Potassium ferricyanide oxidation of salt 1 gave isoquinolinone 7 whose treatment with Grignard reagents resulted in a high-yield formation of substituted isoquinolinium salts 5. The selectivity of the reduction of these salts to give derivatives 6 has been studied. Particularly good selectivities (82-84%) were observed when R is a benzylic group. On the basis of these results, a practical and enantioselective synthesis of the natural alkaloid (-)-argemonine is presented.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Jean-Jacques
authors.initials: JJ
authors.lastname: Youte
authors.forename: Denis
authors.initials: D
authors.lastname: Barbier
authors.forename: Ali
authors.initials: A
authors.lastname: Al-Mourabit
authors.forename: Dino
authors.initials: D
authors.lastname: Gnecco
authors.forename: Christian
authors.initials: C
authors.lastname: Marazano