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Total synthesis of ent-(-)-azonazine using a biomimetic direct oxidative cyclization and structural reassignment of natural product
Alternative TitleTotal synthesis of ent-(-)-azonazine using a biomimetic direct oxidative cyclization and structural reassignment of natural product
Zhao JC(赵吉辰); Yu SM(于顺明); Qiu HB(邱海波); Yao ZJ(姚祝军)
2014
Source PublicationTetrahedron
Volume70Issue:19Pages:3197-3210
AbstractA 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.
Subject Area生命有机化学
DOI10.1016/j.tet.2014.03.061
URL查看原文
Indexed BySCI
Language英语
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/38942
Collection生命有机化学国家重点实验室
Corresponding AuthorYao ZJ(姚祝军)
Affiliation中科院上海有机化学研究所
Recommended Citation
GB/T 7714
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.
APA 赵吉辰,于顺明,邱海波,&姚祝军.(2014).Total synthesis of ent-(-)-azonazine using a biomimetic direct oxidative cyclization and structural reassignment of natural product.Tetrahedron,70(19),3197-3210.
MLA 赵吉辰,et al."Total synthesis of ent-(-)-azonazine using a biomimetic direct oxidative cyclization and structural reassignment of natural product".Tetrahedron 70.19(2014):3197-3210.
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