The reaction of hexa-1,5-dien-3-ols with 2-methyl-1,1,3-triethoxybutane gives unsaturated aldehydes by a Claisen rearrangement which undergo two Cope rearrangements to give 2,5,9-unsaturated aldehydes; the reactions proceed with high stereospecificity when secondary hexa-1,5-dien-3-ols are used, resulting in the 2-trans-5-trans isomer.
R. C. Cookson and N. R. Rogers, J. Chem. Soc., Chem. Commun., 1972, 248 DOI: 10.1039/C39720000248
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