Xylochemistry--Making Natural Products Entirely from Wood.

The first total synthesis of the dimeric berberine alkaloid ilicifoline (ilicifoline B) is reported. Its carbon skeleton is constructed from ferulic acid, veratrole, and methanol. The synthesis reported herein employs starting materials solely derived from wood. The natural product is thus constructed entirely from renewable resources. The same strategy is applied to a formal total synthesis of morphinan alkaloids. The use of wood-derived building blocks (xylochemicals) instead of the conventional petrochemicals represents a sustainable alternative to classical synthetic approaches.

[1]  Jia Guo,et al.  Isolation, identification and antioxidant activity of bound phenolic compounds present in rice bran. , 2015, Food chemistry.

[2]  Jae-Wook Shin,et al.  Isolation and identification of phenolic antioxidants in black rice bran. , 2015, Journal of food science.

[3]  T. Opatz,et al.  A one-pot cascade to protoberberine alkaloids via Stevens rearrangement of nitrile-stabilized ammonium ylides. , 2015, The Journal of organic chemistry.

[4]  T. Opatz,et al.  Enantioselective synthesis of (-)-dihydrocodeine and formal synthesis of (-)-thebaine, (-)-codeine, and (-)-morphine from a deprotonated α-aminonitrile. , 2014, Organic letters.

[5]  T. Opatz,et al.  A high-yielding modular access to the lamellarins: synthesis of lamellarin G trimethyl ether, lamellarin η and dihydrolamellarin η. , 2013, Chemistry.

[6]  C. Freire,et al.  Ultra-high performance liquid chromatography coupled to mass spectrometry applied to the identification of valuable phenolic compounds from Eucalyptus wood. , 2013, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[7]  M. Salem,et al.  Understanding of Formaldehyde Emissions from Solid Wood: An Overview , 2013 .

[8]  C. Supuran,et al.  Synthesis and carbonic anhydrase inhibitory properties of sulfamides structurally related to dopamine. , 2013, Bioorganic & medicinal chemistry.

[9]  T. Fukuyama,et al.  Total synthesis of (-)-morphine. , 2010, Chemistry, an Asian journal.

[10]  M. Eberlin,et al.  Alkaloids from the bark of Guatteria hispida and their evaluation as antioxidant and antimicrobial agents. , 2010, Journal of natural products.

[11]  Arno Behr,et al.  Myrcene as a natural base chemical in sustainable chemistry: a critical review. , 2009, ChemSusChem.

[12]  J. Domínguez,et al.  Ferulic acid and p-coumaric acid solubilization by alkaline hydrolysis of the solid residue obtained after acid prehydrolysis of vine shoot prunings: Effect of the hydroxide and pH , 2009 .

[13]  Aloys Hüttermann,et al.  Sustainable global energy supply based on lignocellulosic biomass from afforestation of degraded areas , 2009, Naturwissenschaften.

[14]  A. J. Hunt,et al.  Green chemistry and the biorefinery: a partnership for a sustainable future , 2006 .

[15]  Frieder W. Lichtenthaler,et al.  Carbohydrates as green raw materials for the chemical industry , 2004 .

[16]  Y. Kita,et al.  Novel and efficient oxidative biaryl coupling reaction of alkylarenes using a hypervalent iodine(III) reagent , 2002 .

[17]  B. Trost,et al.  Enantioselective synthesis of (-)-codeine and (-)-morphine. , 2002, Journal of the American Chemical Society.

[18]  M. J. Manzanos,et al.  Study of the volatile composition of an aqueous oak smoke preparation , 2002 .

[19]  Paul T Anastas,et al.  Origins, current status, and future challenges of green chemistry. , 2002, Accounts of chemical research.

[20]  Jürgen O. Metzger,et al.  10 Jahre nach „Rio“ – Konzepte zum Beitrag der Chemie zu einer nachhaltigen Entwicklung , 2002 .

[21]  Uwe Schneidewind,et al.  10 Years after Rio—Concepts on the Contribution of Chemistry to a Sustainable Development , 2002 .

[22]  W. Friedt,et al.  New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry. , 2000, Angewandte Chemie.

[23]  Hans J. Schäfer,et al.  Neue Synthesen mit Ölen und Fetten als nachwachsende Rohstoffe für die chemische Industrie , 2000 .

[24]  C. Incarvito,et al.  SYNTHESIS OF (-)-ISONITRIN B , 1998 .

[25]  K. Munesada,et al.  Endogenous pine wood nematicidal substances in pines, Pinus massoniana, P. strobus and P. palustris , 1993 .

[26]  H. Blaser.  The Chiral Pool as a Source of Enantioselective Catalysts and Auxiliaries , 1992 .

[27]  C. T. Montgomery,et al.  The protoberberine alkaloids of Stephania suberosa , 1987 .

[28]  T. Hudlický,et al.  Synthesis of morphine alkaloids and derivatives. , 2012, Topics in current chemistry.

[29]  Markus Antonietti,et al.  Chemistry and materials options of sustainable carbon materials made by hydrothermal carbonization. , 2010, Chemical Society reviews.

[30]  P. Schaft.  Chemical Conversions of Natural Precursors , 2007 .

[31]  Thomas J. Colacot,et al.  Chiral chemistry: Mirror, mirror on the wall... who's the fairest molecule of all? , 2001 .

[32]  Hartmut K. Lichtenthaler,et al.  Cell wall bound ferulic acid, the major substance of the blue-green fluorescence emission of plants. , 1998 .

[33]  C. Cárcamo,et al.  Ilicifoline: New Berbine Dimer Alkaloid from Berberis iIicifolia , 1996 .

[34]  H. Morita,et al.  Triterpenes fromMaytenus ilicifolia , 1991 .

[35]  W. Peters,et al.  Product compositions and kinetics in the rapid pyrolysis of milled wood lignin , 1985 .

[36]  M. Polk,et al.  Characterization of the pyrolytic oils , 1980 .