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A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone.

ABSTRACT: Motivated by the biosynthesis of azamerone, we report the first example of a diazo-Hooker reaction, which involves the formation of a phthalazine ring system by the oxidative rearrangement of a diazoketone. Computational studies indicate that the diazo-Hooker reaction proceeds via an 8π-electrocyclization followed by ring contraction and aromatization. The biosynthetic origin of the diazoketone functional group was also chemically mimicked using a related natural product, naphterpin, as a model system.

SUBMITTER: Yahiaoui O

PROVIDER: S-EPMC9006554 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone.

Yahiaoui Oussama O Murray Lauren A M LAM Zhao Fengyue F Moore Bradley S BS Houk Kendall N KN Liu Fang F George Jonathan H JH

Organic letters 20220107 2

Motivated by the biosynthesis of azamerone, we report the first example of a diazo-Hooker reaction, which involves the formation of a phthalazine ring system by the oxidative rearrangement of a diazoketone. Computational studies indicate that the diazo-Hooker reaction proceeds via an 8π-electrocyclization followed by ring contraction and aromatization. The biosynthetic origin of the diazoketone functional group was also chemically mimicked using a related natural product, naphterpin, as a model ...[more]

PMID: 34994200

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