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Paper | Regular issue | Vol 36, No. 11, 1993, pp.2591-2596
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6501
C-Nucleosides. 22. Synthesis of Quinoxaline Acyclo-C-nucleoside

Isamu Maeba,* Masakazu Wakimura, Yasutaka Ito, and Chihiro Ito

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan

Abstract

The synthesis of quinoxaline acyclo-C-nucleoside, 2-[(3S)-3,4-dihydroxybutyl]-3-methylquinoxaline (6), is described. Treatment of furanone glycoisde (1) with 1,2-diaminobenzene gave a mixture of Z- and E- 3-[2-[4-O-benzoyl-(3S)-3-hydroxy-1-butenyl]-3-quinoxalinylmetyl]-1,2,3,4-tetrahydroquinoxalin-2-ones (2a and 2b). Compound (2a) was treated with acetic acid to give three products, Z- and E-2-[4-O-benzoyl-(3S)-3-hydroxy-1-butenyl]-3-methylquinoxalines (3a and 3b) and quinoxalin-2-one (4). Catalytic hydrogenation of 3a,b produced 2-[4-O-benzoyl-(3S)-3-hydroxybutyl]-3-methylquinoxaline (5). Removal of the protecting group in 5 afforded compound (6).