A concise strategy for synthesis of 2-deoxy-d-glucose and its natural product analogues from d-glucose

2-Deoxy-d-glucose (2-DG), an inhibitor of key enzymes in the glycolytic pathway, has broad therapeutic potential and is a part of various natural products. Its 3,6-anhydro backbones are also present in bioactive natural sauropunols. A short and linear synthesis of 2-DG and sauropunols (A-D, F, and H) reported herein, involves conversion of d-glucose-derived 3,5,6-tri-O-benzoyl-1,2-isopropylidene-α-d-glucofuranose to alkyl-3,5,6-tri-O-benzoyl-d-glucofuranosides as the key intermediates through acid-catalyzed glycosylation reaction using three alcohols, followed by Barton-McCombie deoxygenation, cyclization, and appropriate deprotection reactions with excellent functional group tolerance and high yields.