Study on the Regioselectivie of Grignard Reagent Addition Reaction of Maleopimaric Acid Trimethyl Ester

doi:10.6023/cjoc201208006

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (01): 138-142.DOI: 10.6023/cjoc201208006 Previous Articles Next Articles

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马来海松酸三甲酯区域选择性格氏加成反应研究

姚贵阳^a, 韦京辰^a,b, 戴伟龙^a, 杨达^a, 潘英明^a, 王恒山^a

a 广西师范大学化学化工学院药用资源化学与药物分子工程重点实验室桂林 541004;
b 桂林医学院药理学教研室桂林 541004

收稿日期:2012-08-08 修回日期:2012-09-25 发布日期:2012-09-26
通讯作者: 潘英明, 王恒山 E-mail:panym2005@sina.com;wang_hengshan@yahoo.com.cn
基金资助:
973计划前期研究专项(No. 2011CB512005);国家自然科学基金(Nos. 81260472, 21101035);广西自然科学基金重点(No. 2011GXNSFD018010);广西新世纪十百千人才工程人选(No. 2007228)资助项目.

Study on the Regioselectivie of Grignard Reagent Addition Reaction of Maleopimaric Acid Trimethyl Ester

Yao Guiyang^a, Wei Jingchen^a,b, Dai Weilong^a, Yang Da^a, Pan Yingming^a, Wang Hengshan^a

a Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004;
b Department of Pharmacology, Guilin Medical College, Guilin 541004

Received:2012-08-08 Revised:2012-09-25 Published:2012-09-26
Supported by:
Project supported by the Project 973 (No. 2011CB512005), the National Natural Science Foundation of China (Nos. 81260472, 21101035), the Natural Science Foundation of Guangxi Province (No. 2011GXNSFD018010) and the Project of Ten, Hundred, Thousand Distinguished Talents in New Century of Guangxi Province (No. 2007228).

Two regioselectivite adducts (compounds 3 and 4) were firstly synthesized from the Grignard reagent and maleopimaric acid trimethyl ester (2). The structures of all compounds were characterized by elemental analyses, NMR and MS, and stero-structures of 3 were further determined by COSY, HMQC and HMBC. The spatial structure of 3 was further confirmed by X-ray single crystal diffraction analysis method. Owing to the addition reaction selectivity of 2 was dependent on the steric hindrance of three methyl groups, the TADDOL (tetraaryl-1,3-dioxolane-4,5-dimethanols) product was prevented because of the formation of lactone 3, but the stereo-structure of the rosin-ring did not changed. Products of 3 and 4 are expected to apply as chiral derivatization reagents.

Key words: maleopimaric acid trimethyl ester, grignard reagent, 2D NMR, regioselectivity

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Yao Guiyang, Wei Jingchen, Dai Weilong, Yang Da, Pan Yingming, Wang Hengshan. Study on the Regioselectivie of Grignard Reagent Addition Reaction of Maleopimaric Acid Trimethyl Ester[J]. Chin. J. Org. Chem., 2013, 33(01): 138-142.

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马来海松酸三甲酯区域选择性格氏加成反应研究

Study on the Regioselectivie of Grignard Reagent Addition Reaction of Maleopimaric Acid Trimethyl Ester

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