Altersolanol P (AP), a new member of the altersolanol family of compounds, is the inspiration for multiple synthetic studies in our laboratory. The altersolanols, and structurally similar compounds, exhibit antibacterial activity. Recently, we reported our work toward the regioselective synthesis of intermediates en route to altersolanol derivatives via lewis acid catalyzed Diels-Alder reactions of the natural products isoprene and Juglone (5-hydroxy-1,4-naphthalenedione). Epoxidation or dihydroxylation of the resulting adducts is expected to provide a small library of altersolanol derivatives for antibacterial testing. To further expand the molecular diversity of our library, in this study, we will explore the reactivity of 1,4-Naphthoquinone dienophiles with dienes, such as (2E,4E)-2,4-Hexadienyl acetate and 2,4-Hexadien-1-ol. We eventually hope to substitute Juglone (5-hydroxy-1,4-naphthalenedione) for 1,4-Naphtoquinone to explore regioselectivity of the Diels-Alder reaction. New compounds will be tested for antibacterial activity.

Exploring the regioselective Diels-Alder reaction scope of 1,4-naphthoquinones

255th National Meeting (2018)

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