Total Synthesis of Sieboldine A

Previously,
we have finished the total synthesis of lycojaponicumin
A (2) via development of an efficient synthetic strategy
using semipinacol rearrangement as a key step. In order to further
demonstrate the generality of this synthetic route, herein, we report
the total synthesis of another fawcettimine-type alkaloid sieboldine
A (1) from the same intermediate, which possesses an
A/B/D tricyclic ring system and vicinal quaternary centers of 1. The synthesis features late-stage site-selective redox
reactions, Schmidt glycosylation cyclization, and highly selective
transformations.