A scalable synthesis of enantiopure dihydroxyethyl acetamidofuran (Di-HAF) from N-acetylglucosamine (GlcNAc) and valuable insights into the mechanism of the subsequent acid catalysed conjugated dehydration to 3-acetamido-5-acetylfuran (3A5AF).

Furans derived from carbohydrate feedstocks are a versatile class of bio-renewable building blocks and have been used extensively to access 7-oxanorbornenes via Diels-Alder reactions. Due to their substitution patterns these...