Issue 37, 2016

Total synthesis of mangiferin, homomangiferin, and neomangiferin

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

Supplementary files

Article information

Article type
Paper
Submitted
29 Jul 2016
Accepted
22 Aug 2016
First published
22 Aug 2016

Org. Biomol. Chem., 2016,14, 8821-8831

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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