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学科主题: 生命有机化学
题名: Total synthesis of ent-(-)-azonazine using a biomimetic direct oxidative cyclization and structural reassignment of natural product
其他题名: Total synthesis of ent-(-)-azonazine using a biomimetic direct oxidative cyclization and structural reassignment of natural product
作者: Zhao JC(赵吉辰); Yu SM(于顺明); Qiu HB(邱海波); Yao ZJ(姚祝军)
通讯作者: 姚祝军
刊名: Tetrahedron
发表日期: 2014
DOI: 10.1016/j.tet.2014.03.061
卷: 70, 期:19, 页:3197-3210
收录类别: SCI
英文摘要: A biomimetic approach has been investigated and developed for the total synthesis of azonazine, an unusual marine natural cyclopeptide containing a rigid transannular 10-membered ring. A hypervalent iodine-mediated direct oxidative cyclization was successfully developed and applied to construct the highly strained core, which was the key step in the first total synthesis of ent-(-)-azonazine. Based on the physical evidences of synthesized diastereomer and enantiomer of azonazine, both the relative and absolute configurations of the natural product were revised. Two fluorinated azonazine derivatives were also synthesized in short convenient steps utilizing the same intermediate in this work. The established total synthesis opens a potential opportunity to study the structure activity relationship of natural azonazine. (c) 2014 Elsevier Ltd. All rights reserved.
语种: 英语
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/38942
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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作者单位: 中科院上海有机化学研究所

Recommended Citation:
Zhao JC,Yu SM,Qiu HB,et al. Total synthesis of ent-(-)-azonazine using a biomimetic direct oxidative cyclization and structural reassignment of natural product[J]. Tetrahedron,2014,70(19):3197-3210.
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