Novel synthesis of carbohydrate fused α-amino γ-lactams and glycopeptides by NIS mediated ring opening of donor–acceptor substituted cyclopropanes

• Carbohydrate fused α-amino-γ-lactams were synthesized stereoselectively.
• Carbohydrate fused γ-lactams were synthesized.
• An α-amino-γ-lactam was extended to the synthesis of a glucopeptide.

α-Amino γ-lactams have been synthesized from carbohydrate derived cyclopropanecarboxylates using N-iodosuccinimide (NIS) and NaN3. Cyclopropane ring opening with NIS and NaN3 in different solvents has been studied. Reductive cyclization of the intermediate di-azides leads to the carbohydrate fused α-amino γ-lactam and γ-lactams. Additionally, the methodology has been successfully extended to the synthesis of a glycopeptide.

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