STEREOSELECTIVE SYNTHESIS OF TRANS ISOMERS OF A VOLATILE COMPOUND ISOLATED FROM THE ELM BARK BEETLE PTELEOBIUS-VITTATUS VIA STEREOSPECIFIC CYCLODEHYDRATION ROUTE

The stereoselective asymmetric synthesis of two trans isomers of the title natural product, (3R,6R)- and (3S,6S)-tetrahydro-2,2,6-trimethyl-2H-pyran-3-ol, was achieved by starting with easily obtainable ethyl (S)-3-hydroxybutanoate, via the stereospecific asymmetric construction of substituted tetrahydropyran skeletons by the one-step cyclodehydration process of dithioacetal-functionalized chiral 1,5-diols with PPh3 and diethyl azodicarboxylate in THF at room temperature.