Levoglucosenone (LGO) is a relatively complex chiral chemical platform obtained through the catalytic fast pyrolysis of cellulose. The conservation of a natural chiral center procures to this compound a particular interest for the food/feed, cosmetic and pharmaceutical industries. For instance, it can be transferred to synthetize chiral inhibitors of enzymatic reactions occurring in pathogens. Furthermore, the α,β-unsaturated ketone and the protected aldehyde of LGO allow a wide range of chemical reactions.  Previous studies showed that various synthons can be obtained from LGO.  (S)-γ-hydroxymethyl-α,β-butenolide (HBO), (S)-γ-hydroxymethyl-α,β-butyrolactone (2H-HBO) and Cyrene® are probably the most interesting among them since they have many applications in the food/feed and pharmaceutical industries. HBO and 2H-HBO are respectively precursors of drugs and flavors, while Cyrene® is a good substituent for toxic dipolar aprotic solvents such as NMP, DMF or sulfolane.  Different pathways to produce HBO were described in the literature (Koseki and Paris procedures),&lt;span style="font-size:10.8333px"&gt; &lt;/span&gt;but recently Allais <i>et al.</i> developed more efficient and greener pathways giving access to HBO, 2H-HBO and Cyrene®. Despite being efficient in terms of yields and cost, not only these methods can be dangerous to perform - notably at large scale - (<i>i.e</i>., dihydrogen), but the presence of potential metal residues - even in ppm quantities –may also limit their utilizations in certain applications. These drawbacks could thus limit the potential these molecules, specifically in the food/feed, cosmetic and pharmaceutical sectors. To overcome these issues, the use of enzymatic reactions has been considered to overcome these drawbacks. A biocatalytic process involving an alkene reductase has been developed to access both 2H-HBO and Cyrene® with quantitative conversion and yields.

From levoglucosenone to high value synthons: A green access to (S)-γ-hydroxymethyl-α,β-butyrolactone and cyrene®

2019 Spring National Meeting

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