Synthesis of labelled 1-azafagomine

Abstract

(3,4-trans-4,5-trans)-4,5-Dihydroxy-3-(hydroxymethyl)hexahydro-(3-¹³C)pyridazine (azafagomine, 1a) was synthesised in 7 steps starting from (2-¹³C) malonic acid 5a through conversion to pentadienoic acid and Diels–Alder reaction with 4-phenyl-1,2,4-triazole-3,5-dione, reduction, epoxidation, epoxide hydrolysis and deprotection.

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