Total Syntheses of Proposed (±)-Trichodermatides B and C

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Computational Chemistry

Background:

• Trichodermatides B and C are natural products with potential biological significance.
• Previous structural assignments of these compounds exist.
• Total synthesis provides a route to verify natural product structures.

Purpose of the Study:

• To achieve the total synthesis of putative trichodermatides B and C.
• To investigate the structural assignments of trichodermatides B and C using synthesis and computational methods.

Main Methods:

• Utilized an oxa-[3 + 3] annulation strategy for the synthesis.
• Performed Density Functional Theory (DFT) calculations for C13 chemical shifts.
• Synthesized target compounds and their C2-epimers.

Main Results:

• Successfully synthesized compounds B and C, along with their C2-epimers.
• Observed significant spectroscopic differences between synthetic and natural products.
• DFT calculations supported the structures of the synthetic compounds.

Conclusions:

• The synthetic and computational data question the accuracy of the initially proposed structures for trichodermatides B and C.
• Further investigation is warranted to confirm the correct structures of these natural products.