title: The improved synthesis of OPC-29030, a platelet adhesion inhibitor via diastereoselective oxidation of chiral non-racemic sulfide.
abstract: 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 degrees C. The obtained sulfoxide, which diastereomeric excess was easily raised by the recrystallization, could successfully lead to OPC-29030.
authors.affiliation: Department of Materials Chemistry, Graduate School of Engineering, Osaka University, Japan. matsugi@ap.chem.eng.osaka-u.ac.jp
authors.forename: Masato
authors.initials: M
authors.lastname: Matsugi
authors.forename: Rieko
authors.initials: R
authors.lastname: Shimada
authors.forename: Shinji
authors.initials: S
authors.lastname: Ohata
authors.forename: Masatomo
authors.initials: M
authors.lastname: Nojima
authors.forename: Norio
authors.initials: N
authors.lastname: Fukuda
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Minamikawa
authors.forename: Yasuyuki
authors.initials: Y
authors.lastname: Kita
mesh_terms: D007093:Imidazoles; D010084:Oxidation-Reduction; D010973:Platelet Adhesiveness / Q000187:drug effects*; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015363:Quinolones; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds
chemical_list: D007093:Imidazoles; C404198:OPC 29030; D010975:Platelet Aggregation Inhibitors; D015363:Quinolones; D013440:Sulfides; D013457:Sulfur Compounds