Resumen de Aqueous Dearomatization/Diels–Alder Cascade to a Grandifloracin Precursor

Emily A. Shimizu, Brent Cody, Johnson Hoang, Giovanni G. Castro, Michael E. Jung, David A. Vosburg

• A green laboratory experiment has been developed in which students perform an aqueous oxidation/cycloaddition reaction to convert salicyl alcohol into a pentacyclic diepoxydione that is readily isolated by filtration. Drawing on their knowledge of periodate-mediated 1,2-diol cleavage, students propose a mechanism for the oxidation of salicyl alcohol (which is not a 1,2-diol) and the structure of the transient product (prior to a spontaneous Diels–Alder dimerization). Students then characterize salicyl alcohol and their diepoxide product by mass spectrometry, IR spectroscopy, and 1H, 13C, and two-dimensional NMR spectroscopy. The only organic solvents used are small amounts for IR and NMR spectroscopy.