Dess-Martin Oxidation

During the 1980s, hypervalent iodine reagents were developed as selective, mild, and environmentally friendly oxidizing agents for organic synthesis. Perhaps the most important group of these reagents are the periodinanes (derivatives of pentacoordinate iodine (V)), and the most well-known of these include the reagents 2-iodoxybenzoic acid (IBX) and Dess-Martin periodinane (DMP). While IBX had been known since 1893, its insolubility in most organic solvents inhibited its use in organic synthesis. However, in 1983 D.B. Dess and J.C. Martin described the preparation of DMP, a far more soluble alternative. Since this discovery, DMP has become the reagent of choice for the oxidation of alcohols to their corresponding carbonyl compounds, and oxidations using DMP are now known as Dess-Martin oxidations.

In the total synthesis of ustiloxin D, a highly potent inhibitor of microtubule assembly, M.M. Joullié and co-workers utilized DMP to convert a macrocyclic primary alcohol into its corresponding aldehyde.