Concise synthesis of Cannabisin G

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Medicinal Chemistry

Background:

• Cannabisin G is a naturally occurring lignanamide with potential biological activities.
• Efficient synthetic routes are crucial for accessing and studying such compounds.

Purpose of the Study:

• To develop a synthetic strategy for Cannabisin G.
• To establish a high-yielding and regioselective synthesis of the lignanamide.

Main Methods:

• The synthesis started from 3-tert-butyl ethyl ferulate.
• A key step involved oxidative coupling using potassium ferricyanide in alkaline media.
• This method was employed to construct the biphenylbutadiene skeleton.

Main Results:

• Cannabisin G was synthesized with a 45% overall yield.
• The oxidative coupling demonstrated high regioselectivity in forming the target skeleton.
• The synthetic route proved effective for accessing the lignanamide.

Conclusions:

• A viable synthetic pathway for Cannabisin G was established.
• The key oxidative coupling step is efficient and regioselective.
• This synthesis facilitates further research into Cannabisin G's properties.