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.
Key words
natural products - jamtine - total synthesis - one-pot reaction - conjugate reduction
- Robinson cyclization
