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

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-electrocycli...

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Bibliographic Details
Published in:Organic letters 2022-01, Vol.24 (2), p.490-495
Main Authors: Yahiaoui, Oussama, Murray, Lauren A. M, Zhao, Fengyue, Moore, Bradley S, Houk, Kendall N, Liu, Fang, George, Jonathan H
Format: Article
Language:English
Subjects:
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Azo Compounds - chemistry
Biological Products - chemistry
Cyclization
Ketones - chemistry
Molecular Structure
Oxidation-Reduction
Phthalazines - chemical synthesis
Phthalazines - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c03810