Straightforward assembly of the octahydroisoquinoline core of morphinan alkaloids.
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.
Dunet
Julie
J
Université de Bordeaux, Institut des Sciences Moléculaires, UMR-CNRS 5255, 351, cours de la libération, 33405 Talence cedex 05, France.
Lebeuf
Raphaël
R
Bose
Gopal
G
Robert
Frédéric
F
Landais
Yannick
Y
D018360:Crystallography, X-Ray; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry*; D013237:Stereoisomerism
D007546:Isoquinolines; D009019:Morphinans