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

Oussama Yahiaoui, Lauren A.M. Murray, Fengyue Zhao, Bradley S. Moore, Kendall N. Houk, Fang Liu, Jonathan H. George

Research output: Contribution to journalArticleResearchpeer-review

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)490-495
Number of pages6
JournalOrganic Letters
Volume24
Issue number2
DOIs
Publication statusPublished - 21 Jan 2022
Externally publishedYes

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