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Open AccessArticle

Synthesis of a Novel Carbocyclic Analog of Bredinin

Center for Drug Discovery and College of Pharmacy, University of Georgia, Athens, GA 30602, USA
Author to whom correspondence should be addressed.
Molecules 2013, 18(9), 11576-11585;
Received: 23 August 2013 / Revised: 5 September 2013 / Accepted: 10 September 2013 / Published: 17 September 2013
(This article belongs to the Special Issue Synthesis of Nucleosides, Nucleotides and Their Derivatives)
PDF [248 KB, uploaded 18 June 2014]


The natural nucleoside antibiotic, bredinin, exhibits antiviral and other biological activities. While various nucleosides related to bredinin have been synthesized, its carbocyclic analog has remained unknown. Synthesis of this heretofore unknown analog of bredinin is described. The key precursor, (3aS,4R,6R,6aR)-6-((methoxy-methoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine (5), was prepared from the commercially available compound, (1R,4S)-2-azabicyclo[2.2.1] hept-5-en-3-one (4). Our initial approach used intermediate 6, derived in three transformations from 5, for the key photolytic step to produce the desired ring-opened precursor to the target compound. This photochemical transformation was unsuccessful. However, an appropriately protected and related precursor was synthesized from 5 through the following side-chain functional group transformations: elaboration of the amino group through malonyl ester formation, oximation at the central carbon, conversion of ester to amide and catalytic reduction of the oxime group. This precursor, on treatment with triethylorthoformate and catalytic acetic acid in ethanol, underwent cyclization to produce the desired 4-carbamoyl-imidazolium-5-olate ring. Deprotection of the latter product proceeded smoothly to give the carbocyclic analog of bredinin. This target molecule exhibits antiviral activity, albeit low, against a number of RNA viruses. Further biological evaluations are in progress. View Full-Text
Keywords: bredinin; carbocyclic analog; synthesis; intramolecular cyclization; antiviral activity bredinin; carbocyclic analog; synthesis; intramolecular cyclization; antiviral activity

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Nair, V.; Zhang, F. Synthesis of a Novel Carbocyclic Analog of Bredinin. Molecules 2013, 18, 11576-11585.

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