Total Syntheses of Kirkamide and N-acetyl ent-Conduramine B-1

The second total synthesis of recently isolated new C7N aminocyclitol, kirkamide, has been developed. The enantiopure epoxide derived from N-acetylglucosamine in few steps was used as a synthon to accomplish the metal free synthesis of kirkamide and N-acetyl ent-conduramine B-1 in gram scale. The key synthetic steps involve stereoselective epoxidation, acid mediated regioselective epoxide ring opening followed by selective olefination.

Automated summary

The second total synthesis of a newly isolated C7N aminocyclitol, kirkamide, was successfully accomplished. Starting from N-acetylglucosamine, the enantiopure epoxide was used to synthesize kirkamide and N-acetyl ent-conduramine B-1 on a gram scale. Key synthetic steps included stereoselective epoxidation, acid-mediated regioselective epoxide ring opening, and selective olefination.