The first total synthesis of repraesentin F has been accomplished by a highly diastereoselective gold(I)-catalyzed cyclization cascade as the key step. This cycloisomerization/Prins-type tandem transformation enabled direct access to the atypical tricy-clic carbon skeleton of the natural product with the required syn/anti/syn ring fusion. This synthetic effort also allowed reas-signment of the relative configuration of repraesentin F and determination of its absolute configuration.