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. 2015 Mar 18;20(3):4967–4997. doi: 10.3390/molecules20034967

Scheme 22.

Synthesis of the 4'-C-phenyl L-uridine analogues 203 and 204.

Scheme 22

Reagents and Conditions: (i) CH2CHMgBr, THF, 91%; (ii) [Pd2dba3].CHCl3, (1S,2S)- Ligand C, DMAP, dioxane, (CH2CHCH2)3B, rt, 19 h, 33% (ee 87%); (iii) Cl2(PCy3)2RuCHPh, CH2Cl2, rt, 11 h, 86%; (iv)TBDPSCl, imidazole, DMAP, DMF, rt, 45 mn, 97%; (v) [H2Ru(CO)-(PPh3)3], toluene, rt, 70 °C, 4 h and then 80 °C, 9 h, 90%; (vi) PhSeCl, dioxane, bis(trimethylsilyl)uracil, InCl3, rt, 3 h, 67%; (vii) TBAF, THF, rt, 1.5 h, 203:85%, 204:13%.