Synthesis of epoxone from d-fructose. a didactic experiment for organic chemistry laboratory courses focusing on green chemistry principles

摘要

In recent years, the introduction of the Green Chemistry concepts in undergraduate chemistry classes has been intensively pursued. In this regard, the two-step preparation of Epoxone (an organocatalyst developed by Shi ∁ col.) from commercial D-fructose, through ketalization of vicinal diols followed by oxidation of a sterically congested secondary alcohol, involves important topics in Organic Chemistry and employs inexpensive and nontoxic reagents. The reactions are easy to perform and the products from both steps are readily obtained as crystalline solids after simple procedures, thus facilitating their chemical characterization.