Syntheses Of Cis- And Trans-Jamtine And Their N-Oxides Via A Benzyl Configuration-Inversion Approach
SYNLETT(2020)
Abstract
A novel synthesis of the tetrahydroisoquinoline alkaloid jamtine and its epimer is reported. The synthetic strategy hinges on a one-pot conjugate reduction/Robinson cyclization sequence and an efficient benzyl configuration inversion by an oxidation/reduction approach. The N-oxide derivatives of the jamtine isomers were also synthesized and identified by X-ray crystallographic analysis. Additionally, a density functional theory calculation for the four possible N-oxide structures was exploited to gain further insight into the structure of the natural product in comparison to those of the synthetic N-oxides, because the NMR data of the synthetic derivatives did not match those reported for natural jamtine N-oxide.
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Key words
natural products,jamtine,total synthesis,one-pot reaction,conjugate reduction,Robinson cyclization
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