title: Nonracemic Betti base as a new chiral auxiliary: application to total syntheses of enantiopure (2S,6R)-dihydropinidine and (2S,6R)-isosolenopsins.
abstract: Total syntheses of enantiopure alkaloidal natural products (2S,6R)-dihydropinidine (as hydrochloride) and (2S,6R)-isosolenopsins (as hydrochlorides) were achieved in four steps and in 80-82% total yields by using a synthetic strategy of the formation-cleavage of 1,3-oxazinane. (S)-Betti base was proved to be an excellent chiral auxiliary and a novel Pd/C catalyzed N-debenzylation straightforward to amine hydrochloride was developed in the presence of CH2Cl2.
authors.affiliation: Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.
authors.forename: Xinyan
authors.initials: X
authors.lastname: Wang
authors.forename: Yanmei
authors.initials: Y
authors.lastname: Dong
authors.forename: Jianwei
authors.initials: J
authors.lastname: Sun
authors.forename: Xuenong
authors.initials: X
authors.lastname: Xu
authors.forename: Rui
authors.initials: R
authors.lastname: Li
authors.forename: Yuefei
authors.initials: Y
authors.lastname: Hu
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D010880:Piperidines; C409726:dihydropinidine