title: Double reduction of cyclic aromatic sulfonamides: synthesis of (+)-mesembrine and (+)-mesembranol.
abstract: The synthesis of (+)-mesembrine (1) and (+)-mesembranol (2) has been achieved from the monoterpene (S)-(-)-perillyl alcohol. Key transformations include a diastereo- and regioselective Pd-mediated intramolecular Heck reaction, and a double reduction of the resultant cyclic sulfonamide, to afford the cis-3a-aryloctahydroindole skeleton.
authors.affiliation: Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland.
authors.forename: Kimberly
authors.initials: K
authors.lastname: Geoghegan
authors.forename: Paul
authors.initials: P
authors.lastname: Evans
mesh_terms: D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: C583555:3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol; D026121:Indole Alkaloids; C011300:mesembrine