title: Asymmetric synthesis of trisubstituted oxazolidinones by the thiourea-catalyzed aldol reaction of 2-isocyanatomalonate diester.
abstract: A new method has been developed for the synthesis of chiral 4-carboxyl oxazolidinones by the catalytic asymmetric aldol reaction of an isocyanatomalonate diester with an aldehyde in the presence of a thiourea catalyst. The resulting chiral 4-carboxyl oxazolidinones are the equivalent of β-hydroxy-α-amino acids bearing a tri- or tetrasubstituted carbon center at their α position. With this in mind, this procedure was successfully applied to the first total synthesis of mycestericin C, which was completed in 12 steps and represents one of the shortest reported sequences for the construction of natural products of this type.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University , Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Shota
authors.initials: S
authors.lastname: Sakamoto
authors.forename: Naoya
authors.initials: N
authors.lastname: Kazumi
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kobayashi
authors.forename: Chihiro
authors.initials: C
authors.lastname: Tsukano
authors.forename: Yoshiji
authors.initials: Y
authors.lastname: Takemoto
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004537:Eicosanoic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D001688:Biological Products; D004537:Eicosanoic Acids; D023303:Oxazolidinones; C087464:mycestericin C; C116609:3-hydroxybutanal; D013890:Thiourea