Nonracemic Betti base as a new chiral auxiliary: application to total syntheses of enantiopure (2S,6R)-dihydropinidine and (2S,6R)-isosolenopsins.
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.
Wang
Xinyan
X
Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.
Dong
Yanmei
Y
Sun
Jianwei
J
Xu
Xuenong
X
Li
Rui
R
Hu
Yuefei
Y
D000470:Alkaloids / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D010880:Piperidines; C409726:dihydropinidine