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Type: Journal article
Title: A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone
Author: Yahiaoui, O.
Murray, L.A.M.
Zhao, F.
Moore, B.S.
Houk, K.N.
Liu, F.
George, J.H.
Citation: Organic Letters, 2022; 24(2):490-495
Publisher: American Chemical Society
Issue Date: 2022
ISSN: 1523-7052
Statement of
Oussama Yahiaoui, Lauren A. M. Murray, Fengyue Zhao, Bradley S. Moore, Kendall N. Houk, Fang Liu, and Jonathan H. George
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.
Keywords: Oxidation reactions; Biosynthesis; Aromatic compounds; Rearrangement; Aldol reactions
Description: Published: January 7, 2022
Rights: © 2022 American Chemical Society
DOI: 10.1021/acs.orglett.1c03810
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Appears in Collections:Chemistry publications

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