Stereoselective Total Synthesis of Rhodocoranes I and J

Area of Science:

• Organic Chemistry
• Natural Product Synthesis

Background:

• Rhodocoranes are natural products with demonstrated antibacterial, antifungal, and cytotoxic properties.
• The complex structures of rhodocoranes present significant synthetic challenges.

Purpose of the Study:

• To develop a stereoselective total synthesis of rhodocoranes I and J.
• To establish a general synthetic approach for the rhodocorane family.

Main Methods:

• Convergent synthesis strategy.
• Utilized (S)-limonene as a chiral starting material.
• Key steps included hydroboration/oxidation, ozonolysis, aldol condensation, reduction, and palladium-catalyzed allylic transposition.

Main Results:

• Successful stereoselective total synthesis of rhodocoranes I and J.
• Achieved in 10 steps with a 16.4% overall yield.
• Demonstrated the construction of a highly substituted chiral cyclopentanone intermediate.

Conclusions:

• The developed synthetic route provides a general and efficient method for accessing rhodocoranes.
• This work expands the synthetic toolbox for complex natural product synthesis.
• Highlights the utility of chiral pool starting materials in complex molecule construction.