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Paper | Special issue | Vol 84, No. 2, 2012, pp.801-813
Published online, 18th August, 2011
DOI: 10.3987/COM-11-S(P)57
First Synthesis of a Natural Isoxanthopterin Glycoside, Asperopterin-A

Tadashi Hanaya,* Kazumasa Ejiri, and Hiroshi Yamamoto

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

The key precursor, N2-(N,N-dimethylaminomethylene)-6-hydroxymethyl-8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups.