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Development of pharmaceutically relevant bio-based intermediates though aldol condensation and Claisen–Schmidt reactions of dihydrolevoglucosenone (Cyrene®)

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Abstract

Dihydrolevoglucosenone (Cyrene®) has been successfully utilised as a bio-based platform molecule for the synthesis of pharmaceutically relevant intermediates through aldol condensation reactions. Utilising sustainable synthetic methodologies, the self-aldol condensation reaction of Cyrene was achieved in high purity, with isolated yields of 81.3%. Claisen–Schmidt reactions with a range of aromatic and heteroaromatic aldehydes yielded several previously unreported Cyrene-based compounds, characterised by single-crystal X-ray diffraction, FT-IR, NMR and MS.

Graphical abstract: Development of pharmaceutically relevant bio-based intermediates though aldol condensation and Claisen–Schmidt reactions of dihydrolevoglucosenone (Cyrene®)

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Publication details

The article was received on 18 Apr 2018, accepted on 23 May 2018 and first published on 25 May 2018


Article type: Communication
DOI: 10.1039/C8GC01227J
Citation: Green Chem., 2018, Advance Article
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    Development of pharmaceutically relevant bio-based intermediates though aldol condensation and Claisen–Schmidt reactions of dihydrolevoglucosenone (Cyrene®)

    L. Hughes, C. R. McElroy, A. C. Whitwood and A. J. Hunt, Green Chem., 2018, Advance Article , DOI: 10.1039/C8GC01227J

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