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Vibeke Henriette Lauridsen

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

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Catalytic Asymmetric [4+2]‐Cycloadditions Using Tropolones: Developments, Scope, Transformations and Bioactivity. / Hammer, Niels; Erickson, Jeremy David; Lauridsen, Vibeke Henriette; Jakobsen, Joakim Bøgelund; Hansen, Bente Kring; Jacobsen, Kristian Mark; Poulsen, Thomas; Jørgensen, Karl Anker.

In: Angewandte Chemie International Edition, Vol. 57, No. 40, 22.08.2018, p. 13216-13220.

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@article{c472b8e879ac4a8b8aeaab83ea44cce1,
title = "Catalytic Asymmetric [4+2]‐Cycloadditions Using Tropolones: Developments, Scope, Transformations and Bioactivity",
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 Br{\o}nsted‐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.",
author = "Niels Hammer and Erickson, {Jeremy David} and Lauridsen, {Vibeke Henriette} and Jakobsen, {Joakim B{\o}gelund} and Hansen, {Bente Kring} and Jacobsen, {Kristian Mark} and Thomas Poulsen and J{\o}rgensen, {Karl Anker}",
year = "2018",
month = aug,
day = "22",
doi = "10.1002/anie.201808221",
language = "English",
volume = "57",
pages = "13216--13220",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "Wiley-VCH",
number = "40",

}

RIS

TY - JOUR

T1 - Catalytic Asymmetric [4+2]‐Cycloadditions Using Tropolones: Developments, Scope, Transformations and Bioactivity

AU - Hammer, Niels

AU - Erickson, Jeremy David

AU - Lauridsen, Vibeke Henriette

AU - Jakobsen, Joakim Bøgelund

AU - Hansen, Bente Kring

AU - Jacobsen, Kristian Mark

AU - Poulsen, Thomas

AU - Jørgensen, Karl Anker

PY - 2018/8/22

Y1 - 2018/8/22

N2 - 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.

AB - 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.

U2 - 10.1002/anie.201808221

DO - 10.1002/anie.201808221

M3 - Journal article

C2 - 30133090

VL - 57

SP - 13216

EP - 13220

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 40

ER -