Construction of an Isonucleoside on a 2,6-Dioxobicyclo[3.2.0]-heptane Skeleton

Molecules

Yuichi Yoshimura²  Satoshi Kobayashi²  Hitomi Kaneko²  Takeshi Suzuki²  Tomozumi Imamichi¹  Mahesh K. Lakshman³ 

[1] Laboratory of Human Retrovirology, Leidos Biochemical Research Inc., Frederick National Laboratory for Cancer Research, Frederick, MD 21702, USA; E-Mail:;Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan; E-Mails:Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan;

关键词: nucleoside;    bicyclo;    oxetane ring;    conformation;   

DOI  :  10.3390/molecules20034623

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.