Tetrahedron Letters p. 8545 - 8548 (1994)
Update date:2022-08-02
Topics:
Walkup, Robert D.
Mosher, Michael D.
The aldehyde 8 was synthesized in high yield and with excellent stereoselectivity by treating a protected 3-hydroxypropanal with Corey's chiral B-propargyl boradiazoline reagent.Cyclization of this γ-oxoallene with palladium(II) in the presence of methanol and carbon monoxide produced the furanoside 9 with excellent stereoselectivity for the D-deoxyribose geometry.The furanoside 9 was converted to the branched extended sidechain deoxythymidine analog 11 by reduction, protection,and β-stereoselective Vorbruggen coupling.The hydroboration/oxidation of 10 to yield the deoxyribofuranoside analog 13, bearing two sidechain hydroxyl groups, was also demonstrated.
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