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

Area of Science:

• Organic Chemistry
• Catalysis
• Nucleoside Chemistry

Background:

• Tandem catalysis offers efficient synthesis by reducing steps and purification.
• Its application in nucleoside modification remains underexplored.
• Homometallic and multimetallic catalyst systems enable complex molecule construction.

Purpose of the Study:

• To develop novel tandem catalytic protocols for nucleoside modification.
• To provide efficient access to diverse nucleoside analogs.
• To synthesize pharmaceutically relevant compounds and fluorescent molecules.

Main Methods:

• Development of homometallic and multimetallic tandem catalytic protocols.
• One-pot procedures including Sonogashira/cyclization, Heck/Suzuki-Miyaura, amination/amidation, and etherification/Sonogashira coupling/cyclization.
• Synthesis of 5-iododeoxyuridine (5-IdU) derivatives and other nucleoside analogs.

Main Results:

• Successful synthesis of FV-100 and analogs using double tandem Sonogashira/cyclization.
• Creation of fluorescent nucleoside analogs via double tandem Heck/Suzuki-Miyaura and Suzuki-Miyaura cross-coupling.
• Synthesis of a Sangivamycin precursor using double tandem amination/amidation.
• Preparation of BCNA analogs using triple tandem reactions.

Conclusions:

• Tandem catalysis provides an efficient strategy for diverse nucleoside modifications.
• The developed protocols offer access to valuable antiviral drugs and fluorescent compounds.
• This work expands the utility of tandem catalysis in nucleoside chemistry.