Synthesis of novel sugar analogues from levoglucosenone

The development of a sustainable chemical industry will be reliant on the use of biomass derived products for future synthetic needs. One such compound is levoglucosenone, a pyrolytic product of cellulose that has great potential as a chiral synthon and is the focus of this project.<br><br>A useful method for the microwave pyrolysis of cellulose has been developed alongside an inductively heated method with some brief explorations into the separation and quantitative analysis of the resulting bio-oils.<br>A novel microwave-assisted method for the synthesis of oximinoalcohols has been developed that allows deoxy-aminosugars to be synthesised from levoglucosenone in a reliable and consistent manner.

A microwave-assisted Baeyer-Villiger oxidation has been developed which allows for rapid access to a range of substituted chiral butyrolactones with potential for the synthesis of substituted deoxy-nucleoside analogues.<br><br>Synthesis of C-2 aminosugars from oximes of levoglucosenone and derivatives has also been explored. Microwave-assisted epoxidations, which dramatically reduce the reaction time, have also been developed.<br><br>The conjugate addition of phosphorus nucleophiles to levoglucosenone (phospha-Michael addition) to synthesis novel chiral organophosphorus intermediates has also been briefly explored.