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

Niels Hammer; Jeremy David Erickson; Vibeke Henriette Lauridsen; Joakim Bøgelund Jakobsen; Bente Kring Hansen; Kristian Mark Jacobsen; Thomas Poulsen; Karl Anker Jørgensen

doi:10.1002/anie.201808221

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

Niels Hammer, Jeremy David Erickson, Vibeke Henriette Lauridsen, Joakim Bøgelund Jakobsen, Bente Kring Hansen, Kristian Mark Jacobsen, Thomas Poulsen, Karl Anker Jørgensen

Department of Chemistry

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

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.

Original language	English
Journal	Angewandte Chemie International Edition
Volume	57
Issue	40
Pages (from-to)	13216-13220
Number of pages	5
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.201808221
Publication status	Published - 22 Aug 2018

Keywords

bioactivity
cycloaddition
organocatalysis
photoisomerization
tropolone

Access to Document

10.1002/anie.201808221

Cite this

@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 is explored by downstream transformations, including photoisomerizations, and their biological relevancy by in vivo testing in MCF-7 cancer cells.",

keywords = "bioactivity, cycloaddition, organocatalysis, photoisomerization, tropolone",

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 Verlag GmbH & CO. KGaA",

number = "40",

}

Catalytic Asymmetric [4+2]‐Cycloadditions Using Tropolones: Developments, Scope, Transformations and Bioactivity. / Hammer, Niels; Erickson, Jeremy David; Lauridsen, Vibeke Henriette et al.
In: Angewandte Chemie International Edition, Vol. 57, No. 40, 22.08.2018, p. 13216-13220.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

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 is explored by downstream transformations, including photoisomerizations, and their 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 is explored by downstream transformations, including photoisomerizations, and their biological relevancy by in vivo testing in MCF-7 cancer cells.

KW - bioactivity

KW - cycloaddition

KW - organocatalysis

KW - photoisomerization

KW - tropolone

UR - http://www.scopus.com/inward/record.url?scp=85053537532&partnerID=8YFLogxK

U2 - 10.1002/anie.201808221

DO - 10.1002/anie.201808221

M3 - Journal article

C2 - 30133090

SN - 1433-7851

VL - 57

SP - 13216

EP - 13220

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 40

ER -

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this