(+)-Bovidic acid is eighteen-carbon hydroxyfuranoid acid that exhibits activity as an insect repellant and is isolated from the skin of the gaur (Bos frontalis), a bovine native to Southern Asia. We have developed an efficient synthesis of this natural product from (R,R)-hexa-1,5-dien-3,4-diol. Formation of the tetrahydrofuran (THF) ring and appendage of the eastern alkyl side chain are achieved in a single step via size-selective ring-closing/cross metathesis. The western carboxyl-containing side chain is introduced via stereoselective alkylation followed by chemoselective cross metathesis. We expect this strategy will be applicable to the other THF natural products.

Total synthesis of (+)-bovidic acid

255th National Meeting (2018)

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