期刊
TETRAHEDRON
卷 70, 期 19, 页码 3197-3210出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.03.061
关键词
Biomimetic synthesis; Azonazine; Stereochemical assignment; Oxidative cyclization; Hypervalent iodine
资金
- Ministry of Science and Technology of the People's Republic of China [2010CB833200, SS2013AA 090203]
- National Natural Science Foundation of China [21032002]
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.
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