Computational Chemistry Studies of LIGNOLs

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.

[1]  Carl de Boor,et al.  A Practical Guide to Splines , 1978, Applied Mathematical Sciences.

[2]  J. Loike,et al.  Lignans: Chemical, Biological and Clinical Properties , 1990 .

[3]  Berend Smit,et al.  Understanding molecular simulation: from algorithms to applications , 1996 .

[4]  A. Maiti,et al.  Molecular Modeling Techniques In Material Sciences , 2005 .

[5]  P. Eklund,et al.  Structural analysis of sterically hindered 1,4‐diols from the naturally occurring lignan hydroxymatairesinol a quantum chemical study , 2011 .

[6]  Stephen J. Wright,et al.  Numerical Optimization , 2018, Fundamental Statistical Inference.

[7]  Åke Björck,et al.  Numerical Methods , 1995, Handbook of Marine Craft Hydrodynamics and Motion Control.

[8]  David Potter.  Computational physics , 1973 .

[9]  D Vanderspoel,et al.  GROMACS - A PARALLEL COMPUTER FOR MOLECULAR-DYNAMICS SIMULATIONS , 1993 .

[10]  C. W. Gear,et al.  Numerical Integration of Ordinary Differential Equations , 2021, Numerical Methods and Optimization.

[11]  J. M. Watt.  Numerical Initial Value Problems in Ordinary Differential Equations , 1972 .

[12]  Peter M. Kasson,et al.  Gromacs User Manual Version 4.6 , 2013 .

[13]  R W Hockney,et al.  Computer Simulation Using Particles , 1966 .

[14]  A. Leach.  Molecular Modelling: Principles and Applications , 1996 .

[15]  Warren J. Hehre,et al.  AB INITIO Molecular Orbital Theory , 1986 .

[16]  H. Berendsen,et al.  Transport Properties Computed by Linear Response through Weak Coupling to a Bath , 1991 .

[17]  P. Eklund,et al.  Conformational Solvation Studies of LIGNOLs with Molecular Dynamics and Conductor-Like Screening Model , 2012, International journal of molecular sciences.

[18]  C. W. Gear,et al.  Numerical initial value problem~ in ordinary differential eqttations , 1971 .

[19]  J. Brussee,et al.  A highly stereoselective synthesis of s(-)-[1,1′-binaphthalene]-2,2′-diol , 1983 .

[20]  D. Seebach,et al.  Some recent advances in the use of titanium reagents for organic synthesis , 1983 .