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2004
Carbohydrates
U 0500
New Ruthenium-Based Protocol for Cleavage of Terminal Olefins to Primary AlImproved Synthesis of a Bicyclic Nucleoside. — The title method is based
51- 169 cohols:
on RuO4-mediated dihydroxylation, NaIO4-mediated diol cleavage, and NaBH4-mediated reduction. The NaBH4 reduction of the crude reaction mixture obtained after dihydroxylation prevents overoxidation on further periodate treatment. Advantages of
the new method which gives exclusively primary alcohols, are significantly reduced
reaction times compared to osmium- or ozone-based protocols, and no need to work
under anhydrous conditions. Alcohol (IIa) is converted into bicyclic nucleoside (V) via
a tandem reaction cascade for the oxetane ring closure. The debenzylated nucleoside
(V) is thus obtained by a significantly improved synthetic sequence compared to an earlier method in 25% overall yield from alkene (Ia). — (SHARMA, P. K.; NIELSEN*,
P.; J. Org. Chem. 69 (2004) 17, 5742-5745; Dep. Chem., Univ. South. Den., DK-5230
Odense, Den.; Eng.) — Klein
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