Synfacts 2019; 15(09): 1059
DOI: 10.1055/s-0039-1690600
Chemistry in Medicine and Biology
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Synthesis of Pyrimidine Nucleoside Analogs

Dirk Trauner
Andrej Shemet
Trost BM. * Xu S, Sharif EU. Stanford University, USA
New Catalytic Asymmetric Formation of Oxygen Heterocycles Bearing Nucleoside Bases at the Anomeric Carbon.

J. Am. Chem. Soc. 2019;
141: 10199-10204
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20. August 2019 (online)



Many FDA approved antiviral and anticancer drugs contain nucleoside analogs. The biologically active nucleosides are synthesized either by derivatization of an intact nucleoside or by coupling a nitrogenous base with a modified sugar (glycolsylation reaction). However, all previous methods suffered from poor yields and low diastereoselectivities.



Trost and co-workers reported a new Pd-catalyzed synthesis of pyrimidine nucleoside analogs bearing an iodide substituent. This process occurs in high yields as well as excellent enantio- and diastereoselectivity (dr >20:1). The products can be transformed into a variety of new pyrimidine nucleoside analogs. According to the proposed mechanism, the reaction proceeds through a Pd(IV) species, which undergoes reductive elimination to form a C–I bond.