Mittwoch, 20. Oktober 2021 | 10:30 - 11:15

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Levoglucosenone: A sustainable platform chemical from...

Title:«Levoglucosenone: A sustainable platform chemical from waste biomass» Dr. Jason E. Camp, Chief Technology Officer, Circa Group Ltd, 30 Flemington Road , Parkville VIC 3052, Australia, jason.camp@circasc.com https://www.circagroup.com.au/

Circa Group have developed a process for the large-scale conversion of waste cellulose to the bio-privileged molecule levoglucosenone (LGO). This chiral building block has been converted via well-established chemical processes into previously difficult-to-synthesize building blocks such as enantiopure butenolides, dihydropyrans, substituted cyclopropanes, deoxy-sugars and ribonolactones (key scaffolds for COVID-19 drugs; Figure 1). LGO derivatives are used to make a variety of important products including; polymers/plasticiser, agrochemicals, pharmaceuticals and flavours/fragrances. In addition, LGO can be converted into the dipolar aprotic solvent Cyrene™, which has found utility in a variety of different applications in which alternatives to the standard toxic compounds, such as NMP, DMF and DCM, are required. The synthesis, reactivity and utility of LGO derivatives, including Cyrene™, will be presented.

 

References:

For recent articles, reviews and overviews about levoglucosenone and its derivatives, see:
 
(1) Sarotti, A. M.; Zanardi, M. M.; Spanevello, R. A.; Suárez, A. G. Curr. Org. Syn. 2012, 9, 439–459.
(2) Comba, M. B.; Tsai, Y.-h.; Sarotti, A. M.; Mangione, M. I.; Suárez, A. G.; Spanevello, R. A. Eur. J. Org. Chem. 2018, 590–604.
(3) Camp, J. E. ChemSusChem 2018, 11, 3048–3055.
(4) T. W. Bousfield, K. P. R. Pearce, S. B. Nyamini, A. Angelis-Dimakis, J. E. Camp Green Chem. 2019, 21, 3675–3681.
(5) Pan, K.; Fan, Y.; Leng, T.; Li, J.; Xin, Z.; Xin, Z.; Zhang, J.; Hao, L.; Gallop, J.; Novoselov, K. S.; Hu, Z. Nature Comm. 2018, 9, 5197.
(6) 
For an overview on the reactivity of levoglucosenone, see: 
https://circa-group.com/lgo-overview

 

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