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

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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.
OriginalsprogEngelsk
TidsskriftAngewandte Chemie International Edition
Vol/bind57
Nummer40
Sider (fra-til)13216-13220
Antal sider5
ISSN1433-7851
DOI
StatusUdgivet - 22 aug. 2018

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