Total Synthesis of Sieboldine A.

ABSTRACT

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.