Dihydro- and tetrahydrofurans are found in a variety of natural products, including carbohydrates, polyketides, peptides, and terpenoids. Many of these compounds have shown promising biological activities with some being commercially successful drugs. Easily accessible 1,2-dibromohomoallylic alcohols are readily cyclized to 3-bromodihydrofurans using catalytic amounts of inexpensive and abundant Cu (I) salts. These vinylbromides are primed for cross coupling reactions, while the enol ether moiety is amenable to additional transformations, including selective reductions. Our approach to the 1,2-dibromohomoallylic alcohol precursors, the optimization and scope of the cyclization, and further transformation of the 3-bromodihydrofurans will be described.

Copper-mediated cyclization of 1,2-dibromohomoallylic alcohols to versatile 3-bromodihydrofurans

2019 Fall National Meeting

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