Avrainvilleol is a halogenated diarylmethane marine natural product isolated from red algae with significant antibacterial activity. Reported here is the full account of the campaign to prepare avrainvilleol using a transition-metal free cross coupling of a sulfonylhydrazone and boronic acid. Several intial unsuccessful attempts to prepare avrainvilleol and the optimization of the synthesis of the highly substituted hydrazone coupling partner are described.

Application of the transition-metal free cross coupling of sulfonylhydrazones and boronic acids to the total synthesis of avrainvilleol

255th National Meeting (2018)

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