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Thomas Poulsen

Catalytic Asymmetric [4+2]‐Cycloadditions Using Tropolones: Developments, Scope, Transformations and Bioactivity

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DOI

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 are explored by downstream transformations, including photoisomerizations, and biological relevancy by in‐vivo testing in MCF‐7 cancer cells.
Original languageEnglish
JournalAngewandte Chemie International Edition
Volume57
Issue40
Pages (from-to)13216-13220
Number of pages5
ISSN1433-7851
DOIs
Publication statusPublished - 22 Aug 2018

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