Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 40, Pages 13216-13220Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201808221
Keywords
bioactivity; cycloaddition; organocatalysis; photoisomerization; tropolone
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Funding
- Carlsberg Foundation
- Semper Ardens
- Aarhus University
- DNRF
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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 Bronsted-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 invivo testing in MCF-7 cancer cells.
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