There is a large and diverse group of natural and non-natural products containing conjugated polyenes. In this project, we are interested in employing cross metathesis strategy to synthesize the analogues of retinoids and carotenoids which posses 1,3,3-trimethylcyclohexene as part of the conjugated polyene. The cross metathesis using Grubbs ruthenium-based catalysts is widely and successfully applied in the synthesis of biologically active complex compounds. Our synthesis was started with the allylation of beta-cyclocitral with various allyl halides using tin and zinc as metals. Surprisingly both tin and zinc-mediated allylation of beta-cyclocitral afforded the hydroxyl-elimination product as the major product in good yields. The resultant products were purified by flash column chromatography and characterized by using IR and NMR spectroscopic methods. The elimination products of those reactions were then subjected to cross metathesis using Grubbs first generation catalyst. The efforts are underway to determine the biological activities of resultant conjugated polyenes.

Cross metathesis strategy directed towards the synthesis of conjugated polyenes

243rd National Meeting (2012)

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