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学科主题: 生命有机化学
题名: Studies toward the total synthesis of clavulactone
其他题名: 群株虫内酯的全合成研究
作者: Zhu Q(朱强) ; Qiao LQ(乔立群) ; Wu YK(伍贻康) ; Wu YL(吴毓林)
通讯作者: 吴毓林
刊名: J. Org. Chem.
发表日期: 2001
卷: 66, 期:8, 页:2692-2699
收录类别: SCI
部门归属: 中国科学院上海有机化学研究所生命有机化学实验室
英文摘要: Synthetic studies drected toward a total synthesis of clavulactone are reported. In light of the analysis made in our previous wouk, cyclopentane 4a (a key intermediate in the present work) was synthesized through a radical-mediated ring closure of a rationally designed substuate 25. Using HWE reactions, the lower and upper side-chains of 4a were converted into an allyl chloride and an allyl cyanohydrin, respectively. Subsequent treatment of the allyl chloride/cyanohydrin in a highly diluted THF solution with sodium bis(trimethylsiliyl)amide led to intramolecular alkylation and thus completed a major endeavor in synthesizing the dolabellane framework, construction of the eleven-membered ring. SmI^2-mediated lactonization as a model reacion for the formation of the α,β-unsaturated δ-lactone segment of clavulactone is also described.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000168258600021
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/14000
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
Zhu Q,Qiao LQ,Wu YK,et al. Studies toward the total synthesis of clavulactone[J]. J. Org. Chem.,2001,66(8):2692-2699.
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