title: The absolute configuration of (+)-oxopropaline D by theoretical calculation of specific rotation and asymmetric synthesis.
abstract: The specific optical rotations of (R)-oxopropaline D calculated by two ab initio MO methods were +52+/-31 degrees and +61+/-29 degrees, respectively, and (+)-oxopropaline D (3) was presumed to have an R-configuration. On the basis of this theoretical result, the reaction of 1-litio-beta-carboline with (R)-glyceraldehyde acetonide followed by oxidation with MnO(2) gave (R)-oxopropaline D acetonide (4a), which was consistent with the previously synthesized (+)-oxopropaline D acetonide (4) in all respects. From the results of theoretical calculations and the experimental synthesis, we determined that natural (+)-oxopropaline D (3) has an R-configuration.
authors.affiliation: Medicinal Research Laboratory, Taisho Pharmaceutical Co Ltd, Saitama, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kuwada
authors.forename: Miyako
authors.initials: M
authors.lastname: Fukui
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Hata
authors.forename: Tominari
authors.initials: T
authors.lastname: Choshi
authors.forename: Junko
authors.initials: J
authors.lastname: Nobuhiro
authors.forename: Yukio
authors.initials: Y
authors.lastname: Ono
authors.forename: Satoshi
authors.initials: S
authors.lastname: Hibino
mesh_terms: D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry*; D009904:Optical Rotation; D013237:Stereoisomerism
chemical_list: D002243:Carbolines; C085036:oxopropaline D