jo0480444_si_001.pdf (4.84 MB)
Nonracemic Betti Base as a New Chiral Auxiliary: Application to Total Syntheses of Enantiopure (2S,6R)-Dihydropinidine and (2S,6R)-Isosolenopsins
journal contribution
posted on 2005-03-04, 00:00 authored by Xinyan Wang, Yanmei Dong, Jianwei Sun, Xuenong Xu, Rui Li, Yuefei HuTotal 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.