The Barrett group has capitalized on the use of 1,3-dioxin-4-ones 1 to mask β,δ,ζ-triketo-esters for the biomimetic synthesis of resorcylates 2. An underexplored pharmacophore, 2-amino-4-hydroxybenzoic ester 5, is of interest for the development of novel resorcylate natural product derivatives. Herein, we report on the progress towards the synthesis of resorcylate analogs 5, starting from 4-methyl-1,3-oxazin-6-ones 3 via β,δ-diketo-oxazinone 4, using a parallel route to our dioxinone resorcylate synthesis.

Synthesis of 2-amino-4-hydroxybenzoic acid derivatives via biomimetic polyketide aromatization of β,δ-diketo-oxazinones

256th National Meeting (2018)

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