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A variety of chroman spiroketals are synthesized via inverse-demand [4 + 2] cycloaddition of enol ethers and ortho-quinone methides (o-QMs). Low temperature o-QM generation in situ allows for the kinetic, diastereoselective construction of these motifs, providing entry to a number of unusual chroman spiroketal natural products.

Diastereoselective Syntheses of Chroman Spiroketals via [4 + 2] Cycloaddition of Enol Ethers and o-Quinone Methides