title: Synthesis of highly oxidized quinolizidine via reduction of acylpyridinium cations, and total syntheses of quinolizidines 207I and 1-epi-207I.
abstract: A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several functional groups, including carbonyl, silyl, and acetal, were tolerated under mild reaction conditions. The reaction was successfully extended to a one-pot synthesis of a bicyclic compound, and the synthetic strategy was applied to concise total syntheses of quinolizidines 207I and 1-epi-207I, without protecting groups.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto, 606-8501, Japan.
authors.forename: Chihiro
authors.initials: C
authors.lastname: Tsukano
authors.forename: Atsuko
authors.initials: A
authors.lastname: Oimura
authors.forename: Iderbat
authors.initials: I
authors.lastname: Enkhtaivan
authors.forename: Yoshiji
authors.initials: Y
authors.lastname: Takemoto
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002412:Cations; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D002412:Cations; D054837:Quinolizidines