En Route to New Bioactive Compounds from Natural Feedstock: Protection and Reduction of Quinic Acid

The use of biomass-derived compounds allows to utilize cheap chiral molecules as starting materials and create potential drug precursors, among other uses.1-2 This study is based on quinic acid 1, a natural chiral polyol, which is a cheap material and synthetically attractive due to its multiple functional groups.3-4 Quinic acid was transformed into its corresponding lactone and different protecting groups using the tridimensional arrangement of the vicinal diol framework were explored, allowing the preparation of seven different lactone derivatives. Reduction of the lactone exposes a primary hydroxyl functionality that can be further explored due to its higher reactivity. By functionalization/defunctionalization of those hydroxyl groups, a library of different quinic acid derivatives was synthesized and is currently being tested against HT29 human colorectal adenocarcinoma cells.