Total Synthesis of Atrachinenins A and B

Inspired by a new biosynthetic hypothesis, we report a biomimetic total synthesis of atrachinenins A and B that explains their racemic nature. The synthesis exploits an intermolecular Diels-Alder reaction between a quinone meroterpenoid and E-beta-ocimene, followed by intramolecular (3 + 2) cycloaddition and a late-stage aerobic oxidation. Divergent transformations of a simple model system gave several complex polycyclic scaffolds, while also suggesting a structure revision for atrachinenin C.

Automated summary

Inspired by a new biosynthetic hypothesis, a biomimetic total synthesis of atrachinenins A and B was achieved, explaining their racemic nature, and also suggesting a structure revision for atrachinenin C.