Mitsunobu coupling of nucleobases and alcohols: an efficient, practical synthesis for novel nonsugar carbon nucleosides |
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Authors: | Lu Weibing Sengupta Sujata Petersen Jeffrey L Akhmedov Novruz G Shi Xiaodong |
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Institution: | C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA. |
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Abstract: | A simple facile synthesis of substituted purine derivatives has been developed by using Mitsunobu conditions for an alcohol and a respective nucleobase. A wide range of alcohols produces good to excellent yield (>90%). The resulting purine analogues show good regioselectivity with N-9 substitution as the dominant products in most of the cases. Application of diastereospecific alcohols reveals a complete inversion of the carbon stereogenic center giving a single diastereomer. More than two dozen novel nucleobase derivatives have been prepared in high yield. |
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