The first total synthesis of paucidirinine
(1d), a
highly congested aspidofractinine alkaloid containing a special contracted
five-membered lactam ring, was achieved in 10 steps with 8% overall
yield from commercially available materials. Several key maneuvers,
including tandem enamination/[4 + 2] cycloaddition reaction and SmI2-promoted radical cyclization, were featured in this potentially
scalable strategy.
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