Vk. Aggarwal et N. Monteiro, ASYMMETRIC TOTAL SYNTHESIS OF (-CARBOCYCLIC URACIL POLYOXIN-C()), Journal of the Chemical Society. Perkin transactions. I, (17), 1997, pp. 2531-2537
A short, practical, asymmetric synthesis of carbocyclic uracil polyoxi
n C is described, The key step in the synthesis is a regio-and stereo-
selective palladium-mediated substitution reaction of an a-amino subst
ituted unsaturated lactone with bis-silylated uracil, Critical to the
success of this reaction is the use of trimethylsilyl chloride in the
reaction mixture which substantially enhances the reactivity of the la
ctone, The final stages involve dihydroxylation of 1,4-disubstituted c
yclopentene which is essentially non-selective, The factors surroundin
g the poor selectivity of this reaction are discussed.