title: Straightforward assembly of the octahydroisoquinoline core of morphinan alkaloids.
abstract: The octahydroisoquinoline core of morphinan was assembled starting from readily available arylcyclohexadienes. Three different approaches were developed, including a metal- and an acid-mediated Mannich type process and an anionic-mediated cyclization. All provided the desired motif as a single diastereomer having a C9-C13-C14 trans-cis relative configuration.
authors.affiliation: Université de Bordeaux, Institut des Sciences Moléculaires, UMR-CNRS 5255, 351, cours de la libération, 33405 Talence cedex 05, France.
authors.forename: Julie
authors.initials: J
authors.lastname: Dunet
authors.forename: Raphaël
authors.initials: R
authors.lastname: Lebeuf
authors.forename: Gopal
authors.initials: G
authors.lastname: Bose
authors.forename: Frédéric
authors.initials: F
authors.lastname: Robert
authors.forename: Yannick
authors.initials: Y
authors.lastname: Landais
mesh_terms: D018360:Crystallography, X-Ray; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007546:Isoquinolines; D009019:Morphinans