Double intramolecular S(sub N') O-cyclization for stereoselective synthesis of bistetrahydrofuran core of acetogenins

A study was conducted to analyze the synthesis of a C2-symmetric bistetrahydrofuran core of acetogenins by double intramolecular S(sub N') O-cyclization reactions. Sharpless asymmetric dihydroxylation was utilized to carry out the analysis. Results indicated that novel terminal double bonds can be utilized as functional groups for the stepwise elaboration to secondary hydroxyl derivatives.