title: Total synthesis of 8,14-dihydromorphinandienone alkaloids.
abstract: A collective synthesis of 8,14-dihydronorsalutaridine, 8,14-dihydrosalutaridine, norisosinomenine, and isosinomenine is reported. The strategy provides direct access to the correct oxidation level of the products. The combination of an organocatalyst guanidine superbase, a tertiary amine base, and a dehydrating agent was necessary for the successful Henry-Michael-dehydration cascade to form the phenanthrene motif. The required selective aliphatic nitro reduction could only be achieved under heterogeneous transfer-hydrogenation conditions.
authors.affiliation: Department of Chemistry, University of Texas at Austin , 1 University Station A5300, Austin, Texas, 78712, United States.
authors.forename: Bahman
authors.initials: B
authors.lastname: Ghavimi
authors.forename: Philip
authors.initials: P
authors.lastname: Magnus
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D009019:Morphinans / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000588:Amines; D009019:Morphinans; C009271:sinomenine