A straightforward access to functionalizable polymers through ring-opening metathesis polymerization of levoglucosenone-derived monomers

Fadlallah, Sami; Peru, Aurélien; Flourat, Amandine L.; Allais, Florent

doi:10.1016/j.eurpolymj.2020.109980

Cited by 22 publications

(17 citation statements)

References 40 publications

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“…In a quite distinct synthetic application of LGO ( 22 ) and iso ‐LGO ( 24 ), these were each reacted (Scheme 5) with cyclopentadiene (CPD) to give the known Diels‐Alder adducts 38 and 39 , respectively, and these, in turn, subjected to a ring‐opening metathesis polymerisation (ROMP) using the Grubbs’ III catalyst to give polymers 40 and 41 . Co‐polymers and block co‐polymers such as 42 could also be formed by analogous means [39,40] …”

Section: Cellulose Breakdown Products (Platform Molecules)mentioning

confidence: 99%

Exploiting Nature's Most Abundant Polymers: Developing New Pathways for the Conversion of Cellulose, Hemicellulose, Lignin and Chitin into Platform Molecules (and Beyond)

Banwell

Pollard

Liu

et al. 2021

Chemistry An Asian Journal

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The four most prominent forms of biomass are cellulose, hemicellulose, lignin and chitin. In efforts to develop sustainable sources of platform molecules there has been an increasing focus on examining how these biopolymers could be exploited as feedstocks that support the chemical supply chain, including in the production of fine chemicals. Many different approaches are possible and some of the ones being developed in the authors’ laboratories are emphasised.

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Section: Cellulose Breakdown Products (Platform Molecules)mentioning

confidence: 99%

Exploiting Nature's Most Abundant Polymers: Developing New Pathways for the Conversion of Cellulose, Hemicellulose, Lignin and Chitin into Platform Molecules (and Beyond)

Banwell

Pollard

Liu

et al. 2021

Chemistry An Asian Journal

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“…Enantio-, stereo-, regio- and chemoselective reactions have been executed around the core ring-system. These include, 1,6-anhydro ring opening ( Shafizadeh et al, 1979 ; Tagirov et al, 2015 ; Comba et al, 2016 ; Pedersen and Pedersen, 2021 ), Baeyer-Villiger oxidation ( Koseki et al, 1990 ; Koseki et al, 1991 ; Teixeira et al, 2016 ; Bonneau et al, 2018 ; Diot-Neant et al, 2018 ), 1,2-addition ( Shafizadeh and Chin, 1977 ; Tsypysheva et al, 2000 ; Giordano et al, 2012 ; Debsharma et al, 2019 ; Sharipov et al, 2019 ), α-substitution ( Ward and Shafizadeh, 1981 ; Ledingham E. et al, 2017 ; Ledingham E. T. et al, 2017 ; Giri et al, 2017 ; Hughes et al, 2018 ; Liu et al, 2020 ), cycloaddition/cyclization ( Yatsynich et al, 2003 ; Novikov et al, 2009 ; Faizullina et al, 2011 ; Samet et al, 2011 ; Sarotti et al, 2012b ; Banwell et al, 2020 ; Fadlallah et al, 2020 ; Liu et al, 2020 ), and conjugate addition reactions ( Shafizadeh et al, 1982 ; Essig, 1986 ; Samet et al, 1996 ; Trahanovsky et al, 2003 ) ( Figure 1 ). These reactions have led to the controlled synthesis of a multitude of important biologically active motifs, including enantiopure butenolides, dihydropyrans, substituted cyclopropanes, deoxy-sugars and ribonolactones.…”

Section: Introductionmentioning

confidence: 99%

Levoglucosenone: Bio-Based Platform for Drug Discovery

Camp¹,

Greatrex

2022

Front. Chem.

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Levoglucosone (LGO) is a bio-privileged molecule that can be produced on scale from waste biomass. 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. LGO is an excellent starting material for the synthesis of biologically active compounds, including those which have anti-cancer, anti-microbial or anti-inflammatory activity. This review will cover the conversion of LGO to biologically active compounds as well as provide future research directions related to this platform molecule.

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“…Given our strong expertise in levoglucosenone (LGO), a wood-based functional molecule produced at the scale of several tons per year [ 28 , 29 , 30 ], we have recently become interested in developing not only renewable functional monomers and polymers from LGO [ 31 , 32 , 33 , 34 , 35 , 36 ] but also biodegradation protocols to evaluate the end-of-life of our in-house corresponding materials. In this context, we recently reported the first fully renewable citronellol-containing monomers from LGO [ 34 , 35 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Enzymatic Degradation of Sustainable Levoglucosenone-Derived Copolyesters with Renewable Citronellol Side Chains

et al. 2022

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Recently, a renewable five-membered lactone containing citronellol (HBO-citro) was synthesized from levoglucosenone (LGO). A one-pot two-step pathway was then developed to produce a mixture of 5- and 6-membered Lactol-citro molecules (5ML and 6ML, respectively) from HBO-citro. Proton nuclear magnetic resonance (1H NMR) of a mixture of 5ML and 6ML at varying temperatures showed that the chemical shifts of the hydroxyls, as well as the 5ML:6ML ratio, are temperature-dependent. Indeed, a high temperature, such as 65 °C, led to an up-field shielding of the hydroxyl protons as well as a drop in the 5ML:6ML ratio. The monomers 5ML and 6ML were then engaged in polycondensation reactions involving diacyl chlorides. Renewable copolyesters with low glass transition temperatures (as low as −67 °C) and cross-linked citronellol chains were prepared. The polymers were then hydrolyzed using a commercial lipase from Thermomyces lanuginosus (Lipopan® 50 BG). A higher degradation rate was found for the polymers prepared using Lactol-citro molecules, compared to those obtained by the polycondensation reactions of diacyl chlorides with Triol-citro—a monomer recently obtained by the selective reduction of HBO-citro.

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A straightforward access to functionalizable polymers through ring-opening metathesis polymerization of levoglucosenone-derived monomers

Cited by 22 publications

References 40 publications

Exploiting Nature's Most Abundant Polymers: Developing New Pathways for the Conversion of Cellulose, Hemicellulose, Lignin and Chitin into Platform Molecules (and Beyond)

Exploiting Nature's Most Abundant Polymers: Developing New Pathways for the Conversion of Cellulose, Hemicellulose, Lignin and Chitin into Platform Molecules (and Beyond)

Levoglucosenone: Bio-Based Platform for Drug Discovery

Synthesis and Enzymatic Degradation of Sustainable Levoglucosenone-Derived Copolyesters with Renewable Citronellol Side Chains

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