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Issue 37, 2016
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Total synthesis of mangiferin, homomangiferin, and neomangiferin

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Abstract

Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.

Graphical abstract: Total synthesis of mangiferin, homomangiferin, and neomangiferin

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Supplementary files

Article information


Submitted
29 Jul 2016
Accepted
22 Aug 2016
First published
22 Aug 2016

Org. Biomol. Chem., 2016,14, 8821-8831
Article type
Paper

Total synthesis of mangiferin, homomangiferin, and neomangiferin

X. Wei, D. Liang, Q. Wang, X. Meng and Z. Li, Org. Biomol. Chem., 2016, 14, 8821
DOI: 10.1039/C6OB01622G

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