The Absolute Configuration of (+)-Oxopropaline D by Theoretical Calculation of Specific Rotation and Asymmetric Synthesis.
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Accession number;03A0040951
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| Title;The Absolute Configuration of (+)-Oxopropaline D by Theoretical Calculation of Specific Rotation and Asymmetric Synthesis. |
| Author;
KUWADA T
(Taisho Pharmaceutical Co. Ltd., Saitama, Jpn)
FUKUI M
(Fukuyama Univ., Hiroshima, Jpn)
HATA T
(Fukuyama Univ., Hiroshima, Jpn)
CHOSHI T
(Fukuyama Univ., Hiroshima, Jpn)
NOBUHIRO J
(Fukuyama Univ., Hiroshima, Jpn)
ONO Y
(Fukuyama Univ., Hiroshima, Jpn)
HIBINO S
(Fukuyama Univ., Hiroshima, Jpn)
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Journal Title;Chem Pharm Bull
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Journal Code:G0504A
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ISSN:0009-2363
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VOL.51;NO.1;PAGE.20-23(2003)
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| Figure&Table&Reference;FIG.1, TBL.2, REF.12 |
| Pub. Country;Japan |
| Language;English |
| Abstract;The specific optical rotations of (R)-oxopropaline D calculated by two ab initio MO methods were +52.+-.31.DEG. and +61.+-.29.DEG., 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 MnO2 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. (author abst.) |
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