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An iterative acetylene-epoxide coupling strategy for the total synthesis of longimicin C
其他题名An iterative acetylene-epoxide coupling strategy for the total synthesis of longimicin C
He YT(何艳涛); Xue S(薛嵩); Hu TS(胡泰山); Yao ZJ(姚祝军)
2005
发表期刊Tetrahedron Lett.
ISSN0040-4039
卷号46期号:32页码:5393-5397
摘要Longimicin C, a naturally occurring annonaceous acetogenin possessing a C-2-symmetrical bis-THF moiety and a short hydrocarbon chain between its THF-containing region and a terminal gamma-lactone, was synthesized for the first time. The total synthesis was successfully achieved by an iterative acetylene-epoxide coupling strategy. D-Mannitol was used to establish the bis-THF-containing segment, in which the additional stereochemistries were introduced by Sharpless dihydroxylations and intramolecular Williamson etherifications. Regioselective epoxide-openings by the appropriate terminal acetylenes allowed coupling and elaboration of all four fragments including the introduction of three essential hydroxyls into the proper sites of the target skeleton. (c) 2005 Elsevier Ltd. All rights reserved.
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
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收录类别SCI
语种英语
WOS记录号WOS:000230685900033
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被引频次:12[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/331003/21053
专题生命有机化学国家重点实验室
通讯作者Yao ZJ(姚祝军)
推荐引用方式
GB/T 7714
He YT,Xue S,Hu TS,et al. An iterative acetylene-epoxide coupling strategy for the total synthesis of longimicin C[J]. Tetrahedron Lett.,2005,46(32):5393-5397.
APA 何艳涛,薛嵩,胡泰山,&姚祝军.(2005).An iterative acetylene-epoxide coupling strategy for the total synthesis of longimicin C.Tetrahedron Lett.,46(32),5393-5397.
MLA 何艳涛,et al."An iterative acetylene-epoxide coupling strategy for the total synthesis of longimicin C".Tetrahedron Lett. 46.32(2005):5393-5397.
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