An Efficient Stereoselective Synthesis of cis-2,6-Disubstituted Tetrahydropyrans via Gold-Catalyzed Meyer–Schuster Rearrangement/Hydration/oxa-Michael Addition Sequence

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An efficient stereoselective synthesis of cis-2,6-disubstituted tetrahydropyrans 14a–c has been achieved via gold-catalyzed Meyer–Schuster rearrangement/hydration/oxa-Michael addition sequence from bis-propargylic alcohols 13a–c. The reaction of 13a proceeds via 2,6-disubstituted tetrahydropyran 14′a as an intermediate.