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.