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A versatile Diels-Alder approach to functionalized hydroanthraquinones.

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.

SUBMITTER: Beck J

PROVIDER: S-EPMC7735338 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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A versatile Diels-Alder approach to functionalized hydroanthraquinones.

Beck Janina J Fuhr Olaf O Nieger Martin M Bräse Stefan S

Royal Society open science 20201118 11

The synthesis of highly substituted hydroanthraquinone derivatives with up to three stereogenic centres <i>via</i> 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 furth ...[more]

PMID: 33391783

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