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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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Supplementary files

Article information


Submitted
21 Jul 2017
Accepted
26 Aug 2017
First published
30 Aug 2017

This article is Open Access

Green Chem., 2017,19, 4858-4864
Article type
Paper

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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