2-Iodoxybenzoic Acid (IBX) and Dess-Martin Periodinane (DMP)

Recently, 2-iodoxybenzoic acid (IBX 1) [1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide] and Dess-Martin Periodinane (DMP 2) [1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one] {CAUTION!} as oxidants have added glory to a long tradition of hypervalent iodine chemistry. DMP has attracted particular attention as the reagent of choice for oxidation of alcohols to the carbonyl compounds. Mildness, wide functional group tolerance, high yields without over-oxidation, and easy work-up procedure makes them versatile. IBX also oxidizes vic-diols without cleaving the glycol C-C bond, allows oxidative deoximation, oxidative ring closure of amino alcohols to aminals and one pot selective 5′-oxidation/olefination of 2′-deoxynucleosides. Popularity of DMP as a preferred chemoselective oxidant in the plan of total synthesis is reflected by its current use in antifungal polycyclopropane compounds, immunosuppressant sanglifehrin A, potent antitumor agents saponin OSW-1 and macrolide tedanolide.