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Halogenated butyrolactones from the biomass-derived synthon levoglucosenone
Johannes Puschnig1, Martyn Jevric1, Ben W Greatrex1
1Faculty of Medicine and Health, University of New England, Armidale, NSW, 2351, Australia.
None:
Halogenated butyrolactones are found in a variety of bioactive materials and used for the construction of nucleoside analogues. Short procedures for their synthesis have been developed starting with levoglucosenone, which can be obtained in a single step from the pyrolysis of acid-treated cellulose. The processes use inexpensive reagents for the stereoselective C3 functionalization of the bicyclic ring system, with a subsequent Baeyer-Villiger oxidation affording the fluorinated, chlorinated, and brominated dideoxyribonolactones.
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