Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) were prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, meanwhile the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. A ruthenium-based cross-metathesis reaction was used to synthesize new acycloalkenyl nucleosides.