A divergent strategy to the withasomnines

Area of Science:

• Organic Chemistry
• Natural Product Synthesis

Background:

• The withasomnine family comprises pyrazole-based natural products with potential biological activities.
• Previous synthetic approaches have not provided a divergent route to access multiple members of this family.

Purpose of the Study:

• To develop a concise and divergent synthetic strategy for accessing three members of the withasomnine natural product family.
• To establish a novel synthetic route enabling the exploration of structure-activity relationships within this class of compounds.

Main Methods:

• Utilized a regioselective sydnone-alkynylboronate cycloaddition reaction as a key step.
• Employed Suzuki cross-coupling for efficient carbon-carbon bond formation.
• Incorporated silyl group removal for final product deprotection.

Main Results:

• Successfully synthesized three distinct withasomnine natural products.
• Demonstrated the first divergent synthetic approach to this pyrazole-based family.
• The synthetic route proved concise and efficient.

Conclusions:

• The developed synthetic strategy offers a versatile platform for accessing the withasomnine family.
• This work provides valuable insights into the synthesis of pyrazole-based natural products.
• The methodology facilitates further investigation into the biological properties of withasomnine derivatives.