The Improved Synthesis of OPC-29030, a Platelet Adhesion Inhibitor via Diastereoselective Oxidation of Chiral Non-racemic Sulfide

抄録

An improved synthetic route of OPC-29030, the platelet adhesion inhibitor, was established via the diastereoselective oxidation of a chiral non-racemic sulfide (R)-5 to (S_S)-6 by the catalytic oxidation using VO(acac)₂ and cumene hydroperoxide (CHP) in the presence of MS4A. Under the current condition, the diastereoselectivity was not influenced by the presence of moisture, and moderate to high selectivity (72% de) was obtained at −30 °C. The obtained sulfoxide, which diastereomeric excess was easily raised by the recrystallization, could successfully lead to OPC-29030.