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James L. Charlton
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CURRENT ADDRESS
16-912
Tel (250) 743-9857
E-mail charltn@cc.umanitoba.ca
RESEARCH INTERESTS
Dr. Charlton retired in September 2002 and currently is not active in research. He does not supervise students or postdoctoral fellows.
When he was active in research his research interests were
Asymmetric Organic Synthesis
Organic Chemistry; the stereoselective synthesis of lignans; organic synthesis; asymmetric synthesis.
Research interest were in asymmetric organic synthesis, the preparation of enantiomerically pure organic compounds and the study of the mechanism of asymmetric control in organic reactions. He investigated the use of atropisomerism in dibenzylidenesuccinates as a stereochemical tool in the asymmetric synthesis of lignans. He also studied the use of the classic Stobbe reaction, and asymmetric variations therein, in the preparation of lignan natural products. In the past his group studied lactyl and mandyl chiral auxiliaries, in particular, their ability to control asymmetric induction in Diels-Alder reactions and 1,3-dipolar cylcloadditions. Much of the Diels-Alder work involved reactions of o-quinodimethanes with lactyl or mandyl substituted dienophiles in order to develop new methods for the synthesis of lignans.
MOST RECENT PUBLICATIONS
T. Assoumatine, P. K. Datta, T. S. Hooper, B. L. Yvon, J. L. Charlton. A Short Asymmetric Synthesis of (+)-Lyoniresinol Dimethyl Ether. J. Org. Chem. 69, 4140-4144 (2004).
P. K. Datta, C. Yau, T. S. Hooper, B. L. Yvon, J. L. Charlton. Acid-catalysed Cyclization of 2,3-Dibenzylidenesuccinates: Synthesis of Lignans (+/-)-Cagayanin and (+/-)-Galbulin J. Org. Chem., 66, 8606-8611 (2001).
B.L. Yvon, P.K. Datta, T.N. Le, and J.L. Charlton. Synthesis of magnoshinin and cyclogalgravin: Modified Stobbe condensation reaction Synthesis, 1556-1560 (2001).
C. Cow, C. Leung, and J.L. Charlton. Antiviral activity of arylnaphthalene and aryldihydronaphthalene lignans Can. J. Chem., 78, 553-561 (2000).
R. Cai, S.D. Arntfield, J.L. Charlton. Structural changes of sinapic acid during alkali-induced air oxidation and the development of colored substances J. Am. Oil Chem. Soc., 76, 757-764 (1999).
R. Cai, S.D. Arntfield, J.L. Charlton. Structural changes of sinapic acid and sinapine bisulfate during autoclaving with respect to the development of colored substances J. Am. Oil Chem. Soc., 76, 433-441 (1999).
J.L. Charlton, 1998. Antiviral Activity of Lignans. Journal of Natural Products, 61, 1447-1451 (1998).
J.L. Charlton and K-A. Lee. Thomasidioic acid and 6-hydroxy-5,7-dimethoxy-2-naphthoic acid: Are they really natural products? Tetrahedron Letters, 38, 7311-7312 (1997).
D.E. Bogucki and J.L. Charlton. Non-Enzymatic Synthesis of (S)-(-)-Rosmarinic acid and a Study of a Biomimetic Route to (+)-Rabdosiin. Can. J. Chem., 75, 1783-1794 (1997).
J.L. Charlton and G-L. Chee. Asymmetric Synthesis of Lignans using Oxazolidinones as Chiral Auxiliaries. Can. J. Chem., 75, 1076-1083 (1997).
C. Wolf, W.H. Pirkle, C.J. Welch, D.H. Hochmuth, W.A. Konig, G-L. Chee and J.L. Charlton. Determination of the Enantiomerization Barrier of Arylnaphthalene Lignans by Cryogenic Subcritical Fluid Chromatography and Computer Simulation. J. Org. Chem., 62, 5208-5210 (1997).
Rubino, M.I., Arntfield, S.D. and Charlton, J.L. Evaluation of alkaline conversion of sinapic acid to thomasidioic acid. J. Agric. Food Chem., 44, 1399-1402 (1996).
Charlton, J.L., Oleschuk, C.J., and Chee, G-L. Hindered rotation in Arylnaphthalene Lignans. J. Org. Chem., 61, 3452-3457 (1996).
Coltart, D.M. and Charlton, J.L. The asymmetric synthesis of aryltetralin lignans: (-)-Isolariciresinol dimethyl ether and (-)-deoxysikkimotoxin. Can. J. Chem., 74, 88-94 (1996).
Pham, V.C. and Charlton, J.L. Methyl (S)-lactate as a chiral auxiliary in the asymmetric synthesis of Bao Gong Teng A. J. Org. Chem., 60, 8051-8055 (1995).
Rubino, M.I., Arntfield, S.D. and Charlton, J.L. Conversion of phenolics to Lignans: Sinapic acid to thomasidioic acid. J. Am. Oil Chemists' Soc., 72, 1465-1470 (1995).
Charlton, J.L., Bogucki, D. and Guo, P. Unsymmetrical dienophiles and their reactions with ortho-quinodimethanes. Can. J. Chem. 73, 1463-1467 (1995).
Charlton, J.L., Chee G. and McColeman, H. Synthesis of acetylenedicarboxylic acid esters and asymmetric Diels-Alder reactions of the bis(methyl (S)-lactyl) ester. Can. J. Chem., 73, 1454-1462 (1995).
Bogucki, D.E. and Charlton, J.L. An asymmetric synthesis of (-)-Deoxypodophyllotoxin. J. Org. Chem., 60, 588-593 (1995).
Charlton, J.L. and Chee, G. Synthesis of Chiral Esters of Acetylenedicarboxylic Acid. Tetrahedron Letters, 35, 6243-6246 (1994).
Maddaford, S.P. and Charlton, J.L. A general asymmetric synthesis of (-)-a-dimethylretrodendrin and its diastereomers. J. Org. Chem., 58, 4132-4138 (1993).
Charlton, J.L. and Maddaford, S.P. The mechanism of stereoselectivity in the cycloaddition reactions of alpha-hydroxy-ortho-quinodimethanes with the fumarate of methyl lactate and mandelate. Can. J. Chem., 71, 827-833 (1993).
Charlton, J.L., Maddaford, S.M., Koh, K., Boulet, S. and Saunders, M.H. An asymmetric Diels-Alder cycloaddition to alpha-hydroxy-alpha-phenyl-orthoquinodimethane. Tetrahedron: Asymmetry, 4, 645-648 (1993).
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Last updated May 2008 by J. Charlton