Double intramolecular oxymercuration: stereoselective synthesis of highly substituted bis-tetrahydrofuran

Stereoselective intramolecular oxymercuration has been demonstrated as the key reaction for the efficient preparation of mono- and dihydroxylated unsymmetrical bis-tetrahydrofuran skeletons present in naturally occurring biologically active acetogenins using carbohydrates. These trans- and syn-selective intramolecular oxymercurations were explored in an enantioselective synthesis of the bis-tetrahydrofuran skeleton of mucoxin.