Our research focuses on the total synthesis of naturally occurring highly oxidized and densely functionalized carbon skeletons. The generation of dearomatized intermediates and o-quinone methides enable the rapid manipulation and derivatization of aromatic cores. o-Quinone methides in particular undergo a variety of reactions, but in the presence of enol ethers cycloaddition reactions predominate, which enable access to complex spiroketal derivatives. The use of this technology enables the generation of spiroketals in a kinetic fashion, not possible through traditional thermodynamic ketalizations. Herein, we will overview our studies towards finding an appropriate o-quinone methide precursor and demonstrate the application of this methodology towards the total synthesis of paecilospirone, a marine natural product whose unique chroman spiroketal core had not previously been encountered in nature prior to its isolation.