Cyanogenic glycosides (CGs), when enzymatically or hydrolytically cleaved, release HCN as a natural pesticide. Linamarin and Lotaustralin are examples of cyanogenic β-glucosides found in cassava, lima, and other common food plants and seeds. These foodstuffs are toxic and require a tedious preparation process before consumption. In an effort to discover non-lethal pest deterrents, the carbon-linked mimics (β-C-Linamarin (3b) and β-C-Lotaustralin (3c)) have been targeted for synthesis in order to distinguish if structurally isosteric but non-HCN producing glycosides will deter pests. The synthetic route utilizes cross metathesis and oxymercuration strategies to obtain the β-glucoside from known heptenitol (1).

Carbon-linked cyanogenic glycosides as potential non-lethal pesticides

251st National Meeting (2016)

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