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Catalytic Asymmetric [4+2]‐Cycloadditions Using Tropolones: Developments, Scope, Transformations, and Bioactivity
Author(s) -
Hammer Niels,
Erickson Jeremy D.,
Lauridsen Vibeke H.,
Jakobsen Joakim B.,
Hansen Bente K.,
Jacobsen Kristian M.,
Poulsen Thomas B.,
Jørgensen Karl Anker
Publication year - 2018
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.201808221
Subject(s) - scope (computer science) , catalysis , chemistry , combinatorial chemistry , computer science , organic chemistry , programming language
Abstract An organocatalyzed asymmetric [4+2]‐cycloaddition between tropolones and electron‐deficient dienophiles is presented. Complex and biologically interesting dihydrohomobarrelenone scaffolds are formed through a Diels–Alder reaction utilizing bifunctional Brønsted‐base catalysis, affording the corresponding bridged bicyclic cycloadducts in up to quantitative yields with good enantio‐ (up to 92 % ee ) and diastereoselectivity (up to >20:1 d.r.). The synthetic value of the obtained products is explored by downstream transformations, including photoisomerizations, and their biological relevancy by in vivo testing in MCF‐7 cancer cells.