Tetrahedron Letters p. 6755 - 6758 (1994)
Update date:2022-08-05
Topics:
Jung, Michael E.
Gardiner, John M.
The acetylenic alcohol, 3, readily prepared in two steps from propargyl bromide, 1, is converted to methyl 2-deoxy-D-xylofuranoside, 13, and to the unnatural L-enantiomer, 12, in 5 steps and 50% overall yield, utilizing asymmetric dihydroxylation (AD) of alkene 7 for introduction of chirality. A similar strategy from the isomeric Z-allylic alcohol, 4, afforded the 2-deoxy-L-ribofuranoside, but in modest enantiomeric excess.
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