Palladium-Catalyzed Etherification in the Synthesis of bis-Tetrahydrofurans

Significance

The authors present an efficient protocol for the synthesis of substituted bis-tetrahydrofuran systems 2 and 4. The reactivity utilized has already been extensively explored by the group (see Review below) and this report presents an application of this transformation towards targets with more complexity. While alternative protocols also access bis-tetrahydrofurans from diol starting materials (i.e., J. Wang, B. L. Pagenkopf Org. Lett. 2007, 9, 3703), this method may offer advantages since in situ functionalization of the α-positions in the tetrahydrofuran rings is possible.

Review: J. P. Wolfe Synlett 2008, 2913-2937.