A versatile Diels-Alder approach to functionalized hydroanthraquinones.
R Soc Open Sci
; 7(11): 200626, 2020 Nov.
Article
em En
| MEDLINE
| ID: mdl-33391783
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.
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Ano de publicação:
2020
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Article