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.

中文翻译：

---

柯克酰胺和N-乙酰基-对乙酰氨基酚B-1的总合成

已开发出最近分离出的新的C ₇ N氨基环醇，柯尔卡米酰胺的第二种全合成。衍生自对映体纯的环氧化物Ñ乙酰氨基葡萄糖在几个步骤被用作合成子来完成kirkamide和的金属自由合成ñ -乙酰基ENT -conduramine B-1以克规模。关键的合成步骤包括立体选择性环氧化，酸介导的区域选择性环氧化物开环，然后进行选择性烯化。