96(P-8) アキラルなビアリール発色団を用いるキラルアルコールの絶対配置決定法(ポスター発表の部)
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概要
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Since the exciton-coupled circular dichroism (CD) has been extensively applied to various organic compounds to determine their absolute configurations in a nonempirical manner, the CD spectroscopic analysis has been regarded as a reliable tool as X-ray diffraction method for stereochemical elucidation. However, application of this method has been limited to chiral compounds with two or more functional groups. Recently, Harada and co-workers disclosed a novel CD strategy for determinating an absolute configuration of chiral mono-alcohol. We report here a new method to determine absolute configuration of chiral alcohols using achiral diphenic acid derivatives as CD auxiliary. Thus, 5,5'-dinitrodiphenic anhydride 3 was condensed with L-. D-menthol to give methyl esters 5a and 5b after methylation. Their CD spectra did not exhibit an exciton split CD Cotton effect unexpectedly but showed symmetrical CD curves on an x axis. This indicates that chirality of alcohols was effectively transmitted to a biphenyl chromophore. Solvent and substituent effects were studied further. Other chiral alcohols were similarly derivatized with 3. Their CD spectra showed a definite tendency. Alcohols employed are classified into two groups by structural feature (A: unsaturated type; B: saturated type). In group A Cotton effect of (R)-alcohols around 270nm was positive, whereas that of (S)-alcohols was negative. On the other hand, opposite phenomenon was recognized in group B. Practical usefulness of the present method is demonstrated by the determination of absolute configuration of dihydroxybergamottin, isolated from grapefruit juice. The difference CD spectrum of 19 and 20 exhibited a negative Cotton effet around 270-280nm. The configuration was thus assigned to be R.
- 天然有機化合物討論会の論文
- 2000-10-01
著者
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太田 富久
金沢大学大学院医薬保健学研究科(薬学系)天然物化学研究室
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太田 富久
金沢大院薬
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太田 富久
金沢大薬
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細井 信造
金沢大薬
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太田 富久
金沢大 大学院医薬保健学研究科
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神谷 真紀子
金沢大薬
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Ohta T
Faculty Of Pharmaceutical Sciences Tohoku University
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