Total Stereoselective Synthesis of (+)-Goniothalesdiol

The stereoselective synthesis of (+)-goniothalesdiol (1) was accomplished in nine steps starting from commercially available (−)-(2S,3S)-dimethyl d-tartrate (3). The key features were a completely diastereoselective reduction of a β-ketosulfoxide to generate the stereogenic center at C-5 in 7 and formation of the 2,5-cis-substituted tetrahydrofuran ring in 10 from a stereoselective Et3SiH/TMSOTf-promoted reductive cyclization/deoxygenation.