title: Enantioselective approach to functionalized quinolizidines: synthesis of (+)-julandine and (+)-cryptopleurine.
abstract: An efficient synthesis of functionalized quinolizidines was developed from an enantiomerically enriched γ-nitroketone, which is easily prepared by an organocatalytic ketone-nitroalkene Michael addition. Oxidative ring expansion of the nitroketone followed by reductive ring-opening leads to a suitably functionalized nitrodiol which is an intermediate to the title compounds.
authors: Department of Chemistry, Memorial University, St. John's, Newfoundland, Canada. spansare@mun.ca
authors: Sunil V
authors: SV
authors: Pansare
authors: Rajendar
authors: R
authors: Dyapa
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010084:Oxidation-Reduction; D010618:Phenanthrolines / Q000138:chemical synthesis* / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D007659:Ketones; D009574:Nitro Compounds; D010618:Phenanthrolines; D011807:Quinolizines; C508742:julandine; C007160:cryptopleurine