De novo approach to L-anhydrohexitol nucleosides as building blocks for the synthesis of L-hexitol nucleic acids (L-HNA)

A stereoselective and scalable route to 1,5-anhydrohexitol nucleoside analogues belonging to L-series as building blocks for L-HNA oligonucleotide synthesis has been efficiently tuned. Key to the successful outcome of our approach is the development of a DDQ-mediated domino reaction, which leads to the formation of an unsaturated 1,6-anhydrosugar derivative. Sugar elaborations and base insertion then enable to synthesize six-membered nucleosides. (C) 2008 Elsevier Ltd. All rights reserved.