Stereoselective construction of tetra-substituted tetrahydrofuran compounds from benzylic hemiacetal in the presence of H2 and a Pd catalyst: stereoselective synthesis of a stereoisomer of (-)-virgatusin and its antimicrobiological activity.

Tetra-substituted tetrahydrofuran compounds were stereoselectively prepared from benzylic hemiacetal in the neutral condition by employing the simple reagent, H(2), and a Pd catalyst. The stereoselective conversion of benzylic hemiacetal to two different stereoisomers of the tetrasubstituted tetrahydrofuran compound was observed. One of these tetrahydrofuran compounds was converted to the virgatusin stereoisomer to estimate its antimicrobiological activity.