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[reaction: see text] The stereoselective intramolecular reductive etherification of delta-trialkylsilyloxy substituted ketones with catalytic bismuth tribromide and triethylsilane provides a convenient method for the construction of cis-2,6-disubstituted tetrahydropyrans. This method was highlighted in the key step of an expeditious total synthesis of the antibiotic, (-)-centrolobine.

organic letters

Stereoselective Construction of <i>cis</i>-2,6-Disubstituted Tetrahydropyrans <i>via</i> the Reductive Etherification of δ-Trialkylsilyloxy Substituted Ketones: Total Synthesis of (−)-Centrolobine

Stereoselective Construction of cis-2,6-Disubstituted Tetrahydropyrans via the Reductive Etherification of δ-Trialkylsilyloxy Substituted Ketones: Total Synthesis of (−)-Centrolobine