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

Abstract

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. © 2020 Wiley-VCH GmbH