The absolute configuration of (+)-oxopropaline D by theoretical calculation of specific rotation and asymmetric synthesis.
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.
Kuwada
Takeshi
T
Medicinal Research Laboratory, Taisho Pharmaceutical Co Ltd, Saitama, Japan.
Fukui
Miyako
M
Hata
Toshiyuki
T
Choshi
Tominari
T
Nobuhiro
Junko
J
Ono
Yukio
Y
Hibino
Satoshi
S
D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry*; D009904:Optical Rotation; D013237:Stereoisomerism
D002243:Carbolines; C085036:oxopropaline D