Bovidic acid is a tetrahydrofuran natural product isolated from the pelage of Bos frontalis, a bovine native to Asia, with insect repellant activity. We will present our approach to the total synthesis of bovidic acid, which employs tandem ring-closing/cross metathesis as a key step to construct the five-membered oxacycle and install the requisite alkyl side chain in one pot. Stereoselective introduction of the second side chain by allylation will also be discussed. We expect this strategy will be useful for the synthesis of a variety of tetrahydrofuran natural products.

Efforts toward the total synthesis of (+)-bovidic acid

253rd National Meeting (2017)

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