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Issue 20, 2017
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Efficient route for the construction of polycyclic systems from bioderived HMF

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Abstract

The first synthesis of tricyclic compounds from biobased 5-hydroxymethylfurfural (HMF) is described. The Diels–Alder reaction was used to implement the transition from HMF to a non-planar framework, which possessed structural cores of naturally occurring biologically active compounds and building blocks of advanced materials. A one-pot, three-step sustainable synthesis in water was developed starting directly from HMF. The reduction of HMF led to 2,5-bis(hydroxymethyl)furan (BHMF), which could be readily involved in the Diels–Alder cycloaddition reaction with HMF-derived maleimide, followed by hydrogenation of the double bond. The described transformation was diastereoselective and proceeded with a good overall yield. The applicability of the chosen approach for the synthesis of analogous structures containing amine functionality on the side chain was demonstrated. To produce the target compounds, only platform chemicals were used with carbohydrate biomass as the single carbon source.

Graphical abstract: Efficient route for the construction of polycyclic systems from bioderived HMF

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Publication details

The article was received on 21 Jul 2017, accepted on 26 Aug 2017 and first published on 30 Aug 2017


Article type: Paper
DOI: 10.1039/C7GC02211E
Citation: Green Chem., 2017,19, 4858-4864
  • Open access: Creative Commons BY-NC license
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    Efficient route for the construction of polycyclic systems from bioderived HMF

    F. A. Kucherov, K. I. Galkin, E. G. Gordeev and V. P. Ananikov, Green Chem., 2017, 19, 4858
    DOI: 10.1039/C7GC02211E

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