The key Ichikawa/Winstein sequence was initiated by exposing the carbamate 11 to the Ichikawa rearrangement conditions; dehydration to the allyl cyanate and rearrangement to 11b occurred quickly (Scheme 4A). This was followed by equilibration of 11b to a 1:2.5 ratio of 11b:11d via a Winstein rearrangement. The use of VT-NMR spectroscopy to monitor this transformation revealed that the reaction was nearly complete by the time NMR data could be collected. We ultimately found that isolating the intermediate isocyanates 11b and 11d, redissolving the residue in a dilute solution of pentanes and treating it with freshly condensed HNMe2 gave a 51% yield of the desired product 12. Overall, the success of this transformation validated our hypothesis that installation of a group capable of undergoing simultaneous [3,3]-sigmatropic rearrangement prior to the formation of the urea at C1 strategically avoids any intramolecular cross-reactivity at the C2 and C4 positions. Off-target reactivity was reliably controlled using solvent effects and the adjacent C1 and C2 of 12 were successfully set using the first reported example of a tandem Ichikawa/Winstein rearrangement. Scheme 4. Tandem Ichikawa-Winstein rearrangement.