A versatile Diels-Alder approach to functionalized hydroanthraquinones

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http://hdl.handle.net/10138/323375

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Beck , J , Fuhr , O , Nieger , M & Bräse , S 2020 , ' A versatile Diels-Alder approach to functionalized hydroanthraquinones ' , Royal Society Open Science , vol. 7 , no. 11 , 200626 . https://doi.org/10.1098/rsos.200626

Title: A versatile Diels-Alder approach to functionalized hydroanthraquinones
Author: Beck, Janina; Fuhr, Olaf; Nieger, Martin; Bräse, Stefan
Contributor: University of Helsinki, Department of Chemistry
Date: 2020-11-18
Language: eng
Number of pages: 16
Belongs to series: Royal Society Open Science
ISSN: 2054-5703
URI: http://hdl.handle.net/10138/323375
Abstract: 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.
Subject: cycloaddition
natural product
carbocycle
CERCOSPORA-BETICOLA TOXINS
ANTHRAQUINONE
ALTERSOLANOL
INHIBITION
ANNULATION
MOLECULES
PIGMENTS
FUNGI
116 Chemical sciences
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