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

Oussama YahiaouiLauren A M MurrayFengyue ZhaoBradley S MooreKendall N HoukFang LiuJonathan H George
Published in: Organic letters (2022)
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.
Keyphrases
  • cell wall
  • electron transfer