Abstract
Oxymercuration of an enol ether takes place faster than oxymercuration of an isolated alkene. When both functional groups are present in the same molecule, one can use a properly oriented hydroxyl group fixed from the oxymercuration process to participate in a solvomercuration of the second site. This tandem oxymercuration-solvomercuration protocol was applied to the synthesis of two natural products in the 6,8-dioxabicyclo[3.2.1]octane series
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