10.1002/jhet.507
The research investigates the synthesis and reactivity of 3-bromoacetyl-4-hydroxy-6-methyl-2H-pyran-2-one (bromo-DHAA) with various binucleophilic amines. The study begins with the synthesis of bromo-DHAA by reacting dehydroacetic acid (DHAA) with bromine in glacial acetic acid. This compound then reacts with different binucleophilic amines, including alkanediamines, phenylhydrazines, ortho-phenylenediamines, and ortho-aminobenzenethiol, to produce a range of novel heterocyclic products. These products are characterized using IR, 1H and 13C NMR, and mass spectra. The research explores the potential of these compounds for biological activity, with one of the synthesized compounds showing antifungal properties. The study highlights the versatility of bromo-DHAA as a reactive intermediate for generating diverse 2-pyrone derivatives through selective nucleophilic attacks and cyclocondensation reactions.
10.1055/s-0037-1610752
Shuai Wang and George A. Kraus present a novel synthetic route to pogopyrone A using dehydroacetic acid. The authors converted dehydroacetic acid into silyl enol ether and titanium enolate, which reacted efficiently with aldehydes and N-bromosuccinimide. The key step involved the oxidation of the adduct with benzaldehyde using Dess–Martin periodinane (DMP), yielding pogopyrone A with a 78% yield. The study also explored the reactivity of these intermediates with various aldehydes, achieving good yields and scalability. The titanium enolate method was particularly effective, allowing for the synthesis of pogopyrone A in excellent overall yield. The work provides a direct and efficient synthesis of pogopyrone A, contributing to the field of organic synthesis and natural product chemistry.
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