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Synthesis 2015; 47(02): 228-234
DOI: 10.1055/s-0034-1378910
DOI: 10.1055/s-0034-1378910
paper
5′-Noraristeromycin C-Nucleosides Based on Imidazo[1,2-a]pyrazine
Further Information
Publication History
Received: 10 June 2014
Accepted after revision: 03 October 2014
Publication Date:
12 November 2014 (online)
Abstract
The preparation of two C-5′-nor-3-deazaaristeromycin diastereomeric analogues possessing a bridgehead nitrogen is described from (3aR,4R,6S,6aS)-2,2-dimethyl-6-vinyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol that served as the cyclopentyl unit of the target carbocyclic nucleosides and as the scaffold upon which the compounds were built. The process evolved via a de novo approach for constructing the requisite fused imidazo unit between the aforementioned cyclopentyl ring and a readily available 2,3-dichloropyrazine. The syntheses were accomplished in 11 and 8 steps depending on the diastereomer sought.
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