Stereoselective total synthesis of (±)-peribysin E

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Stereoselective Synthesis

Background:

• Peribysin E is a complex natural product with potential biological activity.
• Efficient synthetic routes are crucial for accessing and studying such molecules.

Purpose of the Study:

• To develop a stereoselective synthesis of (±)-peribysin E.
• To explore different strategies for constructing the spiro-lactal moiety.

Main Methods:

• Radical cyclization to form the hydrindanone core.
• Multiple approaches for spiro-lactal annulation, including radical cyclization, acylation, and oxidation.
• Semipinacol-type rearrangement for stereochemical control.

Main Results:

• Three distinct strategies were investigated for spiro-lactal unit annulation.
• The semipinacol rearrangement approach successfully yielded the desired stereochemistry.
• The total synthesis achieved an overall yield of 3.2%.

Conclusions:

• The semipinacol rearrangement is an effective method for constructing the stereodefined spiro-lactal core of peribysin E.
• The developed synthetic route provides access to (±)-peribysin E.
• Further optimization may improve the overall yield.