Total Synthesis of Thuggacin cmc-A and Its Structure Determination

The first total synthesis of thuggacin cmc-A and the determination of the absolute structure are described. The thuggacin family of antibiotics is of great interest due to the antibiotic activity against Mycobacterium tuberculosis. Based on the assumption that seven stereogenic centers in thuggacin cmc-A would share the same stereochemistry as thuggacin-A, all stereogenic centers of thuggacin cmc-A were strictly constructed in a stereocontrolled manner. The total synthesis allowed its stereostructure to be fully confirmed.

Automated summary

This study describes the first total synthesis of thuggacin cmc-A and the confirmation of its absolute structure. The thuggacin family of antibiotics is of interest due to its antibiotic activity against Mycobacterium tuberculosis. Through a stereocontrolled approach, all seven stereogenic centers in thuggacin cmc-A were constructed to match the stereochemistry of thuggacin-A, confirming the stereostructure of the compound.