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Synthesis of novel 3′,4′-seco analogues of didehydro dideoxy nucleosides as potential antiviral agents

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
18
Identifiers
DOI: 10.1016/s0040-4039(00)76665-2

Abstract

Abstract Novel acyclo analogues ( 13, 14) of didehydro dideoxy adenosine (d4A) lacking C-3′C-4′ bond were synthesized as potential anti-HIV agents. The key step involves the bromination of unsaturated isomer 6 with NBS in mono protected ethylene glycol leading to 3′,4′-seco-2′-bromo-3′-hydroxy compound 11a. Activation of 3′-hydroxy group and reductive elimination of vicinal bromo tosylate gave 13 which on deprotection was converted into the target molecule 14.

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