Nitroso-Ene-type Cyclization Toward Diversified Synthesis of Amino Deoxysugars: A Proof of Concept

Amino deoxysugars are abundant in nature and play an important role in various biological functions, promoting numerous efforts to synthesize their structurally unique motifs. In this report, a de novo approach from a readily available lactic acid derivative is devised to construct several amino deoxysugars embedded in natural products, featuring a novel nitroso-ene-type cyclization to introduce a nitrogen atom into the carbon framework. This efficient synthesis provides an unprecedented synthetic route to explore the nitroso-ene cyclization to accumulate intriguing amino deoxysugars.

Automated summary

Amino deoxysugars are widely found in nature and have significant biological functions, leading to numerous attempts to synthesize their unique structures. This study presents a novel approach to constructing amino deoxysugars embedded in natural products from a readily available lactic acid derivative, through a nitroso-ene-type cyclization to introduce a nitrogen atom into the carbon framework. This efficient synthesis provides an unprecedented synthetic route for exploring the nitroso-ene cyclization and accumulating intriguing amino deoxysugars.