An efficient route, starting from but-3-en-1,2-diol, is described to synthesize racemic diastereoisomeric (5-ethoxy-4-vinyl-2,5-dihydrofuran-2-yl) methanol derivatives. Acyclic enyne intermediates having the alkyne moiety directly connected to the asymmetric carbon atom of an acetal were obtained in two steps. These reactive substrates were then subjected to ruthenium-catalyzed enyne metathesis to produce the target compounds in racemic form. The relative configurations were determined by NOE proton NMR experiments. Similar strategy starting from (2S)-but-3-en-1,2-diol was proposed to provide pure enantiomers.
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