N,C-Coupled naphthylisoquinoline alkaloids: a versatile new class of axially chiral natural products.

Covering: up to April 2021During the past decades, a plethora of natural products with restricted rotation about a biaryl axis have been discovered, among them the naphthylisoquinoline (NIQ) alkaloids, mostly C,C-coupled and having remarkable bioactivities. Within this fascinating class of naturally occurring biaryl compounds, NIQ alkaloids bearing an N,C-heterobiaryl axis have attracted particular attention. They are structurally and biosynthetically unprecedented, with interesting stereochemical implications and biological activities. In contrast to existing articles and reviews about axially chiral - yet C,C-coupled - natural products, this is the first, comprehensive review on the new subclass of N,C-coupled NIQs, their isolation and structural elucidation, their N,C-axial chirality, their biosynthetic origin, their promising antiparasitic and antileukemic activities, and their total synthesis.