New ruthenium-based protocol for cleavage of terminal olefins to primary alcohols: improved synthesis of a bicyclic nucleoside.
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.
Sharma
Pawan K
PK
Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, 5230 Odense M, Denmark pon@chem.sdu.dk
Nielsen
Poul
P
D000438:Alcohols / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry*
D000438:Alcohols; D000475:Alkenes; D009705:Nucleosides; D012428:Ruthenium