Construction of an isonucleoside on a 2,6-dioxobicyclo[3.2.0]-heptane skeleton

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Yuichi YoshimuraTomozumi Imamichi

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.

References

Aug 8, 2006·ChemMedChem·D Christopher Meadows, Jacquelyn Gervay-Hague
Dec 15, 2006·Organic Letters·Yuichi YoshimuraHiroki Takahata
Sep 10, 2009·Chemistry : a European Journal·Daniele D'AlonzoPiet Herdewijn
Sep 30, 2009·Journal of Medicinal Chemistry·Youcef Mehellou, Erik De Clercq
May 27, 2010·The Journal of Organic Chemistry·Yuichi YoshimuraHiroki Takahata
Apr 29, 2011·Bioorganic & Medicinal Chemistry Letters·Yuichi YoshimuraHiroki Takahata

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Citations

Jul 18, 2018·Beilstein Journal of Organic Chemistry·Yuichi YoshimuraNoriaki Minakawa

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Methods Mentioned

BETA
NMR
silica
gel column chromatography
column chromatography

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