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A Fused Hexacyclic Ring System: Diastereoselective Polycyclization of 2,4‐Dienals through an Interrupted iso‐Nazarov Reaction
Author(s) -
Marques AnneSophie,
Duhail Thibaut,
Marrot Jérome,
Chataigner Isabelle,
Coeffard Vincent,
Vincent Guillaume,
Moreau Xavier
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201903860
Subject(s) - stereocenter , chemistry , domino , ring (chemistry) , yield (engineering) , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , materials science , metallurgy
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.