An efficient synthesis of optically active [4-13 c] labelled quorum sensing signal autoinducer-2

Abstract

A new synthetic route for the quorum sensing signal Autoinducer-2 (AI-2) is described and used for the preparation of [4-13 C]-AI-2 starting from [1-13 C]-bromoacetic acid. The key step in this process was the enantioselective reduction of an intermediate ketone. This synthesis pro-vides, selectively, both enantiomers of the labelled or unlabelled parent compound, (R) or (S)-4,5-dihydroxypentane-2,3-dione (DPD) and was used for an improved synthesis of [1-13 C]-AI-2.