期刊
TETRAHEDRON
卷 67, 期 35, 页码 6460-6468出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.06.046
关键词
Ravidomycin; Aryl C-glycoside; O -> C-Glycoside rearrangement; [2+2] Cycloaddition; Ring expansion reaction; Total synthesis
资金
- Hayashi Memorial Foundation for Female Natural Scientists
- Tokyo Institute of Technology
- Grants-in-Aid for Scientific Research [22590018, 23000006] Funding Source: KAKEN
Total synthesis of the unnatural enantiomer of deacetylravidomycin M was accomplished. The key steps include, (1) aryl C-glycosidation of the azido-bearing fucosyl acetate 2 by using catalytic Sc(OTf)(3), (2) the [2+2] cycloaddition reaction of alkoxybenzyne bearing an azido sugar to ketene silyl acetal, and (3) the ring expansion reaction of alkoxybenzocyclobutenone. The synthesis revealed that the natural product is not the proposed amine, but the corresponding N-oxide. (C) 2011 Elsevier Ltd. All rights reserved.
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