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学科主题: 天然产物有机化学
题名: Enantioselective total synthesis and correction of the absolute configuration of megislactone
其他题名: Megislactone的对映体选择性全合成
作者: Ren GB(任国宝) ; Wu YK(伍贻康)
通讯作者: 伍贻康
刊名: Tetrahedron
发表日期: 2008
卷: 64, 期:19, 页:4408-4415
收录类别: SCI
部门归属: 中国科学院上海有机所
英文摘要: The title compound, one of the constituents from Iryanthera megistophylla, has been synthesized in enantiopure forms. The stereogenic centers at C-2 and C-3 were constructed by using a chiral auxiliary induced asymmetric aldolization and the C-4 was derived from the corresponding optically active lactates. The carbon-carbon double bond in the side chain was derived from a pure cis vinyl iodide using a Suzuki coupling with an alkyl borane formed in situ from the corresponding terminal alkene. A previously unknown (partial) cis to trans transformation of an isolated C-C double bond in a long alkyl chain was observed during the deprotection of TBS group with CAN. Somewhat unexpectedly, the otherwise undetectable co-presence of the trans isomer of the remote double bond in a long alkyl chain was clearly revealed in H-1 and C-13 NMR in the presence of a lactone ring. The present work unambiguously shows that the absolute configuration of the natural compound is the antipode of the one originally reported. Some errors in the previous H-1 and C-13 NMR sinal assignments are also corrected. (c) 2008 Elsevier Ltd. All rights reserved.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000255585600031
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/20411
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:
Ren GB,Wu YK. Enantioselective total synthesis and correction of the absolute configuration of megislactone[J]. Tetrahedron,2008,64(19):4408-4415.
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