title: Construction of an isonucleoside on a 2,6-dioxobicyclo[3.2.0]-heptane skeleton.
abstract: We have built a new isonucleoside derivative on a 2,6-dioxobicyclo[3.2.0]heptane skeleton as a potential anti-HIV agent. To synthesize the target compound, an acetal-protected dihydroxyacetone was first converted to a 2,3-epoxy-tetrahydrofuran derivative. Introduction of an azide group, followed by the formation of an oxetane ring, gave a pseudosugar derivative with a 2,6-dioxobicyclo[3.2.0]heptane skeleton. The desired isonucleoside was obtained by constructing a purine base moiety on the scaffold, followed by amination.
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. yoshimura@tohoku-pharm.ac.jp.
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Yoshimura
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. s-kobayashi@fujichemical.co.jp.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Kobayashi
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. hitomi.f528@gmail.com.
authors.forename: Hitomi
authors.initials: H
authors.lastname: Kaneko
authors.affiliation: Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. suzutake19851109@coral.plala.or.jp.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Suzuki
authors.affiliation: Laboratory of Human Retrovirology, Leidos Biochemical Research Inc., Frederick National Laboratory for Cancer Research, Frederick, MD 21702, USA. timamichi@mail.nih.gov.
authors.forename: Tomozumi
authors.initials: T
authors.lastname: Imamichi
mesh_terms: D000586:Amination; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006536:Heptanes / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D019380:Anti-HIV Agents; D006536:Heptanes; D009705:Nucleosides