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Open AccessArticle

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

Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan
Laboratory of Human Retrovirology, Leidos Biochemical Research Inc., Frederick National Laboratory for Cancer Research, Frederick, MD 21702, USA
Author to whom correspondence should be addressed.
Academic Editors: Mahesh K. Lakshman and Fumi Nagatsugi
Molecules 2015, 20(3), 4623-4634;
Received: 2 February 2015 / Revised: 3 March 2015 / Accepted: 4 March 2015 / Published: 12 March 2015
(This article belongs to the Special Issue Nucleoside Modifications)
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. View Full-Text
Keywords: nucleoside; bicyclo; oxetane ring; conformation nucleoside; bicyclo; oxetane ring; conformation
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MDPI and ACS Style

Yoshimura, Y.; Kobayashi, S.; Kaneko, H.; Suzuki, T.; Imamichi, T. Construction of an Isonucleoside on a 2,6-Dioxobicyclo[3.2.0]-heptane Skeleton. Molecules 2015, 20, 4623-4634.

AMA Style

Yoshimura Y, Kobayashi S, Kaneko H, Suzuki T, Imamichi T. Construction of an Isonucleoside on a 2,6-Dioxobicyclo[3.2.0]-heptane Skeleton. Molecules. 2015; 20(3):4623-4634.

Chicago/Turabian Style

Yoshimura, Yuichi; Kobayashi, Satoshi; Kaneko, Hitomi; Suzuki, Takeshi; Imamichi, Tomozumi. 2015. "Construction of an Isonucleoside on a 2,6-Dioxobicyclo[3.2.0]-heptane Skeleton" Molecules 20, no. 3: 4623-4634.

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