Contemporary Syntheses of 2-Ketoheptoses and Derivatives

Ketoheptoses are rarely found in Nature, yet early on D-manno-heptulose could be isolated from Avocado. Following detection of D-manno-heptulose to act as an inhibitor of glucokinase the involvement of ketoheptoses in biomedical applications required synthetic approaches. This review focuses on syntheses of ketoheptoses by rearrangement reactions (de Bruyn-van Ekenstein, Amadori, Bilik) as well as chain elongation reactions (Henry, Grignard, exocyclic enolethers) and gives an overview of the synthetic activity from early syntheses to most recent improvements.