A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4-Dienals through an Interrupted iso-Nazarov Reaction

Abstract

We report an unprecedented domino polycyclization from readily available 2,4-dienals and cyclic α,β-unsaturated imines that is initiated by an iso-Nazarov reaction. This Brønsted acid promoted reaction enables the concomitant formation of four bonds, three cycles, and four contiguous stereogenic centers to yield elaborated structures in a single operation. A range of fused hexacyclic molecules is obtained in a highly diastereoselective manner.

Keywords: diversity-oriented synthesis; domino reactions; iso-Nazarov reaction; pericyclic reactions; polycyclization.