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Molecules 2015, 20(3), 4623-4634;

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
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)
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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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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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.

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