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Total synthesis of (±)-auranthine confirmed its refined structure.

ABSTRACT: Auranthine, isolated in 1986 from Penicillium aurantiogriseum, is a fungal benzodiazepine. Through the successful total synthesis of (±)-auranthine, we confirmed the refined structure of natural (-)-auranthine. We established that natural (-)-auranthine is a fused quinazolino benzodiazepine dione 1 featuring an acyclic aliphatic nitrile moiety, thereby disproving the proposed structure 2.

SUBMITTER: Reinker M

PROVIDER: S-EPMC10766008 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Total synthesis of (±)-auranthine confirmed its refined structure.

Reinker Marie M Kalinina Svetlana A SA Kalinin Dmitrii V DV

RSC advances 20240104 3

Auranthine, isolated in 1986 from <i>Penicillium aurantiogriseum</i>, is a fungal benzodiazepine. Through the successful total synthesis of (±)-auranthine, we confirmed the refined structure of natural (-)-auranthine. We established that natural (-)-auranthine is a fused quinazolino benzodiazepine dione 1 featuring an acyclic aliphatic nitrile moiety, thereby disproving the proposed structure 2. ...[more]

PMID: 38179097

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