In this presentation, cyclization reactions that have been developed for α-hydroxymethyl cyclopropanes using Lewis acid catalysts will be discussed. Recently, these α-hydroxymethyl cyclopropanes, derived from donor-acceptor cyclopropanes, have been shown to undergo dehydrative, ring opening cyclizations through the use of a calcium catalyst, resulting in functionalized 1-aryl-1,2-dihydronaphthalenes. These core structures are a subset of a large pool of plant natural products known as lignans. In addition, chemodivergence for α-hydroxymethyl cyclopropanes was observed, providing access to α-alkylidene-γ-butyrolactones. These combined methodologies establish α-hydroxymethyl cyclopropanes as a strong template for diversity-oriented synthesis, accessing two different types of biologically active core structures from identical, easily accessible starting materials.<br/>

Acid-catalyzed cyclizations of α-hydroxymethyl cyclopropanes

253rd National Meeting (2017)

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