Absolute Configuration Determination for Natural Products(Ⅰ)——Absolute Configuration Determination for Ketone, Lactone and Alcohol by Comparing Computed Optical Rotations and  13C NMR with the Experimental Results

Chem. J. Chinese Universities ›› 2011, Vol. 32 ›› Issue (11): 2568.

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Absolute Configuration Determination for Natural Products(Ⅰ)——Absolute Configuration Determination for Ketone, Lactone and Alcohol by Comparing Computed Optical Rotations and 13C NMR with the Experimental Results

SHEN Lan^1,2, ZHAO Sheng-Ding¹, ZHU Hua-Jie^1*

1. Organic Synthesis and Natural Product Laboratory, State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China;
2. Graduate School of the Chinese Academy of Sciences, Beijing 100049, China

Received:2010-11-26 Revised:2011-01-04 Online:2011-11-10 Published:2011-10-14
Contact: ZHU Hua-Jie E-mail:hjzhu@mail.kib.ac.cn
Supported by:
国家“九七三”计划项目(批准号: 2009CB522300), 国家自然科学基金(批准号: 30770235, 30873141)和昆明植物研究所植物化学与西部资源国家重点实验室资助.

Abstract

Abstract: Optical rotation and 13C NMR computations for five natural products, vidalenolone(1), 2-(3-dihydroxy-3-methylbutyl)benzene-1,4-diol(2), 5,6,7,7a(S)-tetrahydro-2-hydroxy-1-(p-hydroxyphenyl)-3H-pyrolizin-3-one(3), 3,4-dihydro-4,8-dihydroxy-6-methoxy-7-methyl-1(2H-|naphthalenone(4) and 6-(R)-(4'-oxopentyl)-5,6-dihydro-2H-pyran-2-one(5), were performed at the B3LYP/aug-cc-pVDZ//B3LYP/6-31G(d) levels for assigning their absolute configurations. The computational results matched the experimental results well. One compound's 13C NMR chemical shifts were corrected based on the computational 13C NMR results and earliest reports.

Key words: Natural product, Density functional theory, Optical rotation, 13C NMR computation, Absolute configuration determination

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SHEN Lan, ZHAO Sheng-Ding, ZHU Hua-Jie*. Absolute Configuration Determination for Natural Products(Ⅰ)——Absolute Configuration Determination for Ketone, Lactone and Alcohol by Comparing Computed Optical Rotations and 13C NMR with the Experimental Results[J]. Chem. J. Chinese Universities, 2011, 32(11): 2568.

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Absolute Configuration Determination for Natural Products(Ⅰ)——Absolute Configuration Determination for Ketone, Lactone and Alcohol by Comparing Computed Optical Rotations and 13C NMR with the Experimental Results

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