A versatile Diels–Alder approach to functionalized hydroanthraquinones

A versatile Diels–Alder approach to functionalized hydroanthraquinones

The synthesis of highly substituted hydroanthraquinone derivatives with up to three stereogenic centres via a Diels–Alder reaction, starting from easily accessible 2-substituted naphthoquinones, is described. The [4+2]-cycloaddition is applicable for a broad range of substrates, runs under mild cond...

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Main Authors: Janina Beck, Olaf Fuhr, Martin Nieger, Stefan Bräse
Format: Article
Language:English
Published: The Royal Society 2020-11-01
Series:Royal Society Open Science
Subjects:
cycloaddition
natural product
carbocycle
Online Access:https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.200626
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spelling doaj-0847a92c48e6404c96f338b4293bf76f2021-01-15T15:05:37ZengThe Royal SocietyRoyal Society Open Science2054-57032020-11-0171110.1098/rsos.200626200626A versatile Diels–Alder approach to functionalized hydroanthraquinonesJanina BeckOlaf FuhrMartin NiegerStefan BräseThe synthesis of highly substituted hydroanthraquinone derivatives with up to three stereogenic centres via a Diels–Alder reaction, starting from easily accessible 2-substituted naphthoquinones, is described. The [4+2]-cycloaddition is applicable for a broad range of substrates, runs under mild conditions and results in high yields. The highly regioselective outcome of the reactions is enabled by a benzoyl substituent at C2 of the dienophiles. The obtained hydroanthraquinones can be further modified and represent ideal substrates for follow-up intramolecular coupling reactions to create unique bicyclo[3.3.1] or -[3.2.2]nonane ring systems which are important natural product skeletons.https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.200626cycloadditionnatural productcarbocycle
collection DOAJ
language English
format Article
sources DOAJ
author Janina Beck
Olaf Fuhr
Martin Nieger
Stefan Bräse
spellingShingle Janina Beck
Olaf Fuhr
Martin Nieger
Stefan Bräse
A versatile Diels–Alder approach to functionalized hydroanthraquinones
Royal Society Open Science
cycloaddition
natural product
carbocycle
author_facet Janina Beck
Olaf Fuhr
Martin Nieger
Stefan Bräse
author_sort Janina Beck
title A versatile Diels–Alder approach to functionalized hydroanthraquinones
title_short A versatile Diels–Alder approach to functionalized hydroanthraquinones
title_full A versatile Diels–Alder approach to functionalized hydroanthraquinones
title_fullStr A versatile Diels–Alder approach to functionalized hydroanthraquinones
title_full_unstemmed A versatile Diels–Alder approach to functionalized hydroanthraquinones
title_sort versatile diels–alder approach to functionalized hydroanthraquinones
publisher The Royal Society
series Royal Society Open Science
issn 2054-5703
publishDate 2020-11-01
description The synthesis of highly substituted hydroanthraquinone derivatives with up to three stereogenic centres via a Diels–Alder reaction, starting from easily accessible 2-substituted naphthoquinones, is described. The [4+2]-cycloaddition is applicable for a broad range of substrates, runs under mild conditions and results in high yields. The highly regioselective outcome of the reactions is enabled by a benzoyl substituent at C2 of the dienophiles. The obtained hydroanthraquinones can be further modified and represent ideal substrates for follow-up intramolecular coupling reactions to create unique bicyclo[3.3.1] or -[3.2.2]nonane ring systems which are important natural product skeletons.
topic cycloaddition
natural product
carbocycle
url https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.200626
work_keys_str_mv AT janinabeck aversatiledielsalderapproachtofunctionalizedhydroanthraquinones
AT olaffuhr aversatiledielsalderapproachtofunctionalizedhydroanthraquinones
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AT stefanbrase aversatiledielsalderapproachtofunctionalizedhydroanthraquinones
AT janinabeck versatiledielsalderapproachtofunctionalizedhydroanthraquinones
AT olaffuhr versatiledielsalderapproachtofunctionalizedhydroanthraquinones
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AT stefanbrase versatiledielsalderapproachtofunctionalizedhydroanthraquinones
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