Synthesis of Fluorinated Ketoheptoses as Specific Diagnostic Agents

The straightforward syntheses of six regioisomeric mono‐ and difluorinated D‐manno‐heptulose and Kamusol analogues, which use electrophilic or nucleophilic fluorinaton, are reported. D‐manno‐Heptulose shows attractive pharmacological properties in vivo, such as antitumour activity, as well as binding to and accumulating in pancreatic beta cells to induce hyperglycemia. The synthesised analogues represent promising probes for the detection and quantification of beta cells in vivo by 19F MRI techniques, which could help to investigate disease progression. In addition, they are potential candidates for the inhibition of tumour growth. The syntheses of several new fluorinated analogues of D‐manno‐heptulose were achieved by using electrophilic and nucleophilic fluorinating agents. The future use of these analogues in diabetes diagnostics that investigate disease progression by 19F MRI techniques as well as their activity against various types of cancer is discussed.