Synthesis of Sparsomycin via Regioselective Oxidation of Disulfide Intermediate Employing Titanium–Mandelate Complex

Abstract The total synthesis of sparsomycin, a natural bioactive compound with both antitumor and antibiotic activities, was achieved using a titanium–mandelate complex that regioselectively oxidizes one of the sulfide moieties in a synthetic intermediate containing a disulfide structure. This oxidation process exhibited a regioselectivity of 73:27, preferentially oxidizing the sterically hindered sulfur atom at the desired internal position. Using the single diastereomer of the purified monosulfoxide, the synthesis of sparsomycin was then accomplished.