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Computational Chemistry Studies of LIGNOLs

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Part of the book series: Lecture Notes in Computer Science ((LNTCS,volume 7782))

Abstract

The forest industries are developing new innovative products in addition to the traditional bulk products. A promising raw material for added-value products consists of lignans that are extracted in chemical pulping from residual knots. The anticarcinogenic and antioxidative lignan hydroxymatairesinol (HMR) is found in large amounts in the knots of Norway spruce (Picea abies). It has been used in the synthesis of TADDOL-like α-conidendrin-based chiral 1,4-diols (LIGNOLs) [1] with the same functionality as TADDOLs [5] or BINOLs [2], which are often used as ligands for transition metal catalysed asymmetric synthesis. They have hindered structures containing two adjacent stereocenters, resulting in a fixed angle between the metal-complexing hydroxyl groups.

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References

  1. Brusentsev, Y., Sandberg, T., Hotokka, M., Sjöholm, R., Eklund, P.: Synthesis and structural analysis of sterically hindered chiral 1,4-diol ligands derived from the lignan hydroxymatairesinol. Accepted in Tetrahedron Lett. (2012)

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  2. Brussee, J., Jansen, A.C.A.: A highly stereoselective synthesis of s(-)-[1,1’-binaphthalene]-2,2’-diol. Tetrahedron Lett. 24, 3261–3262 (1983)

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  3. Sandberg, T., Brusentsev, Y., Eklund, P., Hotokka, M.: Structural analysis of sterically hindered 1,4-diols from the naturally occurring lignan hydroxymatairesinol. a quantum chemical study. Int. J. Quantum Chem. 111, 4309–4317 (2011)

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  4. Sandberg, T., Eklund, P., Hotokka, M.: Conformational solvation studies of lignols with molecular dynamics and conductor-like screening model. Int. J. Mol. Sci. 13, 9845–9863 (2012)

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  5. Seebach, D., Beck, A.K., Schiess, M., Widler, L., Wonnacott, A.: Some recent advances in the use of titanium reagents for organic synthesis. Pure Appl. Chem. 55, 1807–1822 (1983)

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© 2013 Springer-Verlag Berlin Heidelberg

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Sandberg, T., Eklund, P., Hotokka, M. (2013). Computational Chemistry Studies of LIGNOLs. In: Manninen, P., Öster, P. (eds) Applied Parallel and Scientific Computing. PARA 2012. Lecture Notes in Computer Science, vol 7782. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-36803-5_45

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  • DOI: https://doi.org/10.1007/978-3-642-36803-5_45

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-36802-8

  • Online ISBN: 978-3-642-36803-5

  • eBook Packages: Computer ScienceComputer Science (R0)

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