Journal
ORGANIC LETTERS
Volume 8, Issue 26, Pages 6015-6018Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol062491j
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A novel method for synthesizing isonucleosides, a new class of anti-HIV nucleosides, is described. 2,2- Dimethyl- 1,3- dioxan- 5- one was converted into a dioxabicyclohexane derivative in six steps. After cleaving the epoxide group with thiophenol, the resulting product was subjected to the Mitsunobu reaction in the presence of a nucleobase to give the desired isonucleoside derivative via migration of the thiophenyl group. Removal of the thiophenyl group under radical conditions followed by deprotection led to the 4'- substituted 2', 3'- dideoxyisonucleosides as a racemic mixture.
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