A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2, 4‐Dienals through an Interrupted iso‐Nazarov Reaction. Issue 29 (24th June 2019)

• Record Type: Journal Article
• Authors: Marques, Anne‐Sophie; Duhail, Thibaut; Marrot, Jérome; Chataigner, Isabelle; Coeffard, Vincent; Vincent, Guillaume; Moreau, Xavier
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 29(2019)
• Page Start: 9969
• Page End: 9973
• Publication Date: 2019-06-24
• Subjects: diversity-oriented synthesis -- domino reactions -- iso-Nazarov reaction -- pericyclic reactions -- polycyclization; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201903860
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Ring, ring, ring : An unprecedented domino polycyclization from readily available 2, 4‐dienals and cyclic α, β‐unsaturated imines, initiated by an iso‐Nazarov reaction, is reported. This Brønsted acid promoted transformation affords original polycyclic scaffolds and enables the formation of three new cycles, four new bonds, and four contiguous stereocenters in a single operation and in a highly diastereoselective manner.