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学科主题: 生命有机化学
题名: On the synthesis of cepacin A
其他题名: 葱茎菌素甲的合成研究
作者: Tang CJ(唐朝军) ; Wu YK(伍贻康)
通讯作者: 伍贻康
刊名: Tetrahedron
发表日期: 2007
卷: 63, 期:23, 页:4887-4906
收录类别: SCI
部门归属: 上海有机所
英文摘要: Efforts directed toward a total synthesis of cepacin A is presented in full detail. The C-7, C-8, and C-9 stereogenic centers in the target molecule were derived from D-arabinose. The configuration of the allene axis was controlled at the bromoallenation step by the C-10 configuration of the precursor. An unexpected yet very interesting phenomenon was observed with the bromoallenation, where the alpha-isomer of the propargylic alcohol 31 was entirely resistant to the conditions that worked so well for its beta-counterpart. The problem was eventually solved by careful tuning of the size of the neighboring groups based on the clue obtained from conformational analysis. The diyne moiety was incorporated into the molecular framework through a coupling of the TMS protected diyne with a proper bromoallene under the Sonogashira conditions with EtOAc as the solvent. Use of other solvents at this step led to complete failure. (c) 2007 Elsevier Ltd. All rights reserved.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000248238600005
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/20391
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:
Tang CJ,Wu YK. On the synthesis of cepacin A[J]. Tetrahedron,2007,63(23):4887-4906.
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