Total Synthesis of Nortopsentin D via a Late-Stage Pinacol-like Rearrangement

Nortopsentin D is part of a class of bis(indole) alkaloids known for their biological activity, including inhibitory activity in tumoral cells and antifungal activity. Herein we describe the first total synthesis of nortopsentin D, in which amidine and dione undergo a pivotal condensation and subsequent cyclization via a pinacol-like rearrangement. This synthesis represents a unique strategy for the formation of 5,5-disubstituted (4H)-imidazol-4-one containing natural products, many of which have yet to succumb to total synthesis.

Automated summary

The study presents the first total synthesis of Nortopsentin D, involving a pivotal condensation and subsequent cyclization of amidine and dione via a pinacol-like rearrangement. This unique synthetic strategy is significant for the formation of 5,5-disubstituted (4H)-imidazol-4-one containing natural products.