| Summary: | (2<i>S</i>,3<i>R</i>,6<i>R</i>)-2-[(<i>R</i>)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2<i>H</i>-pyran-3-ol was isolated in 18% after treating the glucose derived (5<i>R</i>,6<i>S</i>,7<i>R</i>)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1<i>S</i>)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.
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