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



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

  1. 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;
  • 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 Guiyanga, Wei Jingchena,b, Dai Weilonga, Yang Daa, Pan Yingminga, Wang Hengshana   

  1. 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