Tandem Homometallic or Multimetallic Catalysis for Assembly of Base-Modified Nucleosides

Abstract

Tandem catalysis has been at the forefront of synthesis in the past decade due to the reduction in the number of steps and purification needed for the synthesis of commercially relevant molecules. With the right combination of catalyst systems, which could be homometallic or multimetallic, one can construct complex structural motifs in a one-pot procedure without the requirement for the isolation of the intermediates, reducing both reagent waste and time. Over the years, application of tandem catalysis has certainly extended towards arene and heteroarene motifs; nucleoside modification using such a strategy has been rare. In this regard, we would like to report herein the development of numerous homometallic and multimetallic tandem catalytic protocols for the modification of nucleosides, providing efficient access to a diverse range of molecules with promising fluorescent properties, as well as pharmaceutically relevant antiviral drugs such as FV-100. © 2020 Wiley Periodicals LLC.

Basic Protocol 1: Double tandem one-pot Sonogashira/cyclization of 5-IdU for the synthesis of FV-100 and analogs

Basic Protocol 2: Double tandem one-pot Heck/Suzuki–Miyaura of 5-IdU for the synthesis of fluorescent nucleoside analogs

Basic Protocol 3: Double tandem one-pot Suzuki–Miyaura cross-coupling of 5-IdU for the synthesis of fluorescent nucleoside analogs

Basic Protocol 4: Double tandem one-pot amination/amidation for the synthesis of Sangivamycin precursor

Basic Protocol 5: Triple tandem one-pot chemoselective etherification/Sonogashira coupling/cyclization for synthesis of BCNA analogs

Basic Protocol 6: Triple tandem one-pot sequential Heck/borylation/Suzuki-Miyaura reaction