The total synthesis of (-)-nitidasin

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Medicinal Chemistry

Background:

• Nitidasin is a pentacyclic sesterterpenoid with a unique 5-8-6-5 carbon skeleton.
• It is derived from Hercampuri, a Peruvian folk medicine.
• Nitidasin belongs to a small group of sesterterpenoids characterized by an isopropyl trans-hydrindane moiety.

Purpose of the Study:

• To report the first total synthesis of Nitidasin.
• To establish a general synthetic strategy for related natural products.

Main Methods:

• A convergent synthetic route was employed.
• Key steps included stereoselective addition of an alkenyl lithium compound to a trans-hydrindanone.
• Chemoselective epoxidation, ring-closing olefin metathesis, and redox adjustment were utilized.

Main Results:

• The total synthesis of Nitidasin was successfully accomplished.
• The developed stereoselective and convergent route is efficient.

Conclusions:

• The total synthesis of Nitidasin opens avenues for further investigation of its biological activities.
• This work represents a significant advancement in the synthesis of complex sesterterpenoids.