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Chemistry of tonghaosu analogs: Novel acid-catalyzed nucleophilic addition to the dienyl acetal system
其他题名茼蒿素类似物的化学: 新的酸催化的对二烯缩酮系统的亲核加成反应
Yin BL(尹标林); Wu WM(吴文敏); Hu TS(胡泰山); Wu YL(吴毓林)
2003
发表期刊Eur. J. Org. Chem.
ISSN1434-193X
期号20页码:4016-4022
摘要The acid-catalyzed nucleophilic addition reaction of spiroketal enol ether-containing toghaosu analogs 2 was explored. Soft nucleophilies, such as mercaptans, alcohols and heteroaromatic compounds, gave rise exclusively to 1,6-adducts, while harder nucleophiles, such as Grignard reagents, afforded mixtures of 1,2-and 1,6-adducts. The reaction with cysteine and glutathione, which might be related to the mode cysteine and glutathione, which might be related to the mode of action of insect antifeeding, also took place smoothly. Friedel-Crafts dimerization reactions of 10 and 11 gave the dimers 12 and 13 respectively. By comparison of ~1HNMR spectroscopic data, we also suggest that the structure of compound 9 reported in the literature for a natural product is revised to that of compound 13.
学科领域生命有机化学
部门归属中国科学院上海有机化学研究所生命有机国家重点实验室
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收录类别SCI
语种英语
WOS记录号WOS:000186162200019
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被引频次:7[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/14054
专题生命有机化学国家重点实验室
通讯作者Wu YL(吴毓林)
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GB/T 7714
Yin BL,Wu WM,Hu TS,et al. Chemistry of tonghaosu analogs: Novel acid-catalyzed nucleophilic addition to the dienyl acetal system[J]. Eur. J. Org. Chem.,2003(20):4016-4022.
APA 尹标林,吴文敏,胡泰山,&吴毓林.(2003).Chemistry of tonghaosu analogs: Novel acid-catalyzed nucleophilic addition to the dienyl acetal system.Eur. J. Org. Chem.(20),4016-4022.
MLA 尹标林,et al."Chemistry of tonghaosu analogs: Novel acid-catalyzed nucleophilic addition to the dienyl acetal system".Eur. J. Org. Chem. .20(2003):4016-4022.
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