New ruthenium-based protocol for cleavage of terminal olefins to primary alcohols: improved synthesis of a bicyclic nucleoside |
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Authors: | Sharma Pawan K Nielsen Poul |
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Affiliation: | Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, 5230 Odense M, Denmark pon@chem.sdu.dk |
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Abstract: | A new protocol for the oxidative cleavage of terminal alkenes to give exclusively primary alcohols in high yields is introduced. The protocol is based on RuO4-mediated dihydroxylation, NaIO4-mediated diol cleavage, and NaBH4-mediated reduction, but the introduction of a reducing step before the diol cleavage removes the formation of byproducts and improves the yield significantly. The new protocol has been developed and used for the improved preparation of a [3.2.0]bicycloarabinonucleoside with important potential in antisense and antigene technology. |
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