The direct synthesis of N3 substituted pyrimidine nucleoterpenes from uridine, thymidine, and inosine with C5, C10, and C15 side chains and using DBU as the base is described. In all cases the reaction proceeded smoothly in very good yields (85–99%) affording selectively N3 substituted adducts.
KrutzfeldJ., RajewskiN., BraichR., RajevK.G., TuschlT., ManoharanM., StoffelM. (2005) Silencing of microRNAs in vivo with 'antagomirs. Nature, 438, 685–689.
2.
ManoharanM., InamatiG., TivelK.L., ConklinB., RossB.S., CookP.D. (1997) 2′- and 3′-Cholesterol-conjugated adenosine and cytosine nucleoside building blocks: synthesis of lipidic nucleic acidsNucleosides Nucleotides, 16, 1141–1144.
3.
Diaz-MarreroA.R., AustinP., Van SoestR., MatainahoT., RoskelleyC.D., RobergeM., AndersenR.J. (2006) Avinosol, a meroterpenoid-nucleoside conjugate with antiinvasion activity isolated from the marine sponge Dysidea sp. Organic Letters, 8, 3749–3752.
IlanE.Z., TorresM.R., PrudhommeJ., Le RochK., JensenP.R., FenicalW. (2013) Farnesides A and B, sesquiterpenoid nucleoside ethers from a marine-derived Streptomyces sp., strain CNT-372 from Fiji. Journal of Natural Products, 76, 1815–1818.
6.
DumelinC.E., ChenY., LeconteA.M., ChenY.G., LiuD.R. (2012) Discovery and biological characterization of geranylated RNA in bacteriaNature Chemical Biology, 8, 913–919.
7.
KostlerK., WerzE., MaleckiE., Montilla-MartinezM., RosemeyerH. (2013) Nucleoterpenes of thymidine and 2′-deoxyinosine: synthons for a biomimetic lipophilization of oligonucleotidesChemistry and Biodiversity, 10, 39–61.
8.
CuriniM., EpifanoF., MalteseF., MarcotullioM.C., Prieto GonzalesS., RodriguezJ.C. (2003) Synthesis of collinin, an antiviral coumarin. Australian Journal of Chemistry, 56, 59–62.
