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

Anne-Sophie Marques (1) , Thibaut Duhail , Jérôme Marrot (1) , Isabelle Chataigner (2, 3) , Vincent Coeffard (4) , Guillaume Vincent (5) , Xavier Moreau (1)

1 ILV - Institut Lavoisier de Versailles
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
3 LCT - Laboratoire de chimie théorique
4 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation
5 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay

An unprecedented iso-Nazarov initiated domino polycyclization from readily available 2,4-dienals and cyclic ,unsaturated imines is reported. 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.

Domaines: Chimie; Chimie organique

Anne-Sophie Marques, Thibaut Duhail, Jérôme Marrot, Isabelle Chataigner, Vincent Coeffard, et al.. A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4-Dienals through an Interrupted iso-Nazarov Reaction. Angewandte Chemie International Edition, 2019, 58 (29), pp.9969-9973. ⟨10.1002/anie.201903860⟩. ⟨hal-02322633⟩