Synthesis of Nucleosides and Deoxynucleosides via Gold(I)-Catalyzed N -Glycosylation of Glycosyl ( Z )-Ynenoates

作者：Rongkun Liu, Yan Chen, Jibin Zheng, Lvfeng Zhang, Tong Xu, Peng Xu, You Yang · 发表于：Organic Letters · 年份：2022 · DOI：10.1021/acs.orglett.2c03964 · 被引用次数：34 · 研究领域：Carbohydrate Chemistry and Synthesis、Catalytic Alkyne Reactions、African history and culture studies

Nucleoside analogues are widely used as anticancer and antiviral drugs. Here, we develop a highly efficient gold(I)-catalyzed N -glycosylation approach for versatile synthesis of various types of nucleosides and deoxynucleosides with glycosyl ( Z )-ynenoates as donors. The wide scope of the N -glycosylation approach was demonstrated by the synthesis of 31 pyrimidine nucleosides and 8 purine nucleosides. Remarkably, the gold(I)-catalyzed N -glycosylation of pyranosyl ( Z )-ynenoates with purines was found to be very effective for regioselective synthesis of pyranosyl N9 purine nucleosides. Based on the catalytic N -glycosylation approach, convenient synthesis of two 5′-deoxynucleosides drugs (capecitabine and galocitabine), four 2′-deoxynucleoside drugs (floxuridine, trifluridine, decitabine and cladribine), four 3′,5′-dideoxynucleoside analogues, and four 2′,5′-dideoxynucleoside analogues was achieved in a collective manner.