Total Synthesis of Racemic Benzomalvin E, a Quinazolinone Isolated from Pencilium sp . FN070315 and Exploration to the Direct Synthesis of ( E )-Benzomalvin B.

We present the first total synthesis of (±) benzomalvin E, featuring a quinazolino moiety with a 6-6-6-7-fused tetracyclic skeleton containing three nitrogen atoms. The key transformation involves Cu-catalyzed intramolecular C-N arylation of quinazolinone, leading to a sclerotigenin analogue that undergoes nucleophilic addition with benzaldehyde, enabling the synthesis of (±) benzomalvin E in six linear steps with a 33% overall yield. The (±) benzomalvin E's structure was validated by 2-D NMR and single crystal XRD analysis and was further transformed into ( E )-benzomalvin B.