John N. Marx

Associate Professor

Ph.D., University of Kansas, 1965

Postdoctoral Study, Cambridge University, 1966

Postdoctoral Study, Johns Hopkins University, 1967

Phone: (806) 742-3082

Fax: (806) 742-1289

Organic Chemistry

Professor Marx's research interests are broad, with the major emphasis on the total synthesis natural products. In addition, he does substantial collaborative work in such diverse fields as pharmaceutical research and custom syntheses of analytical reagents.

The major goal in the synthesis of natural products is to design short and hopefully efficient total syntheses of compounds of the sesquiterpene class, using modern synthetic reactions and as much ingenuity as possible to keep the syntheses short. Another goal is to develop new reactions or new applications of existing reactions.

Some specific target molecules under investigation or planned include occidenol (1), phytuberin (2), aplysistatin (3).

The molecules represent respectively a compound with a unique functional group (dioxipin or seven-membered divinyl ether), a compact three dimensional but acid-sensitive structure which acts as a toxic principle, and a marine bromine-containing compound which has substantial anticancer activity .

The second area of research involves detailed mechanistic study of the fundamental process whereby electron withdrawing substituents such as carbethoxy undergo 1,2-migrations in cationic rearrangement reactions.

These substituents are polarized such that the carbon atom actually migrating bears partial positive charge density, yet is called upon to stabilize further positive charge in the transition state of the migration.

Professor Marx has made substantial progress in understanding such rearrangement reactions since his pioneering paper [J.A.C.S, 96, 2121 (1974)]. Recent work has led to an hypothesis which suggests strongly that one can predict not only which group will migrate in a specific system, but also how fast it will migrate. Extensive checking of the hypothesis is being done, by placing electron-withdrawing groups in migratory competition with simple and aryl groups in a number of rearranging systems, and by investigating the behavior of a number of electron withdrawing groups, such as esters, thioesters, amides, nitrites, nitro groups, etc.

Selected Publications

"Facile, Efficient Conjugation of a Trifunctional Lanthanide Chelate to a Peripheral Benzodiazepine Receptor Ligand," Manning, H. C.; Goebel, T.; Marx, J. N.; Bornhop, D. J., Organic Lett. 2002, 4, 1075-1078.
"Simple, High Yielding Synthesis of Trifunctional Fluorescent Lathanide Chelates," Griffin, J. M. M.; Skwierawska, A. M.; Manning, H. C.; Marx, J. N.; Bornhop, D. J., Tetrahedron Lett. 2001, 42, 3823-3825.
"A Stereoselective Total Synthesis of (-)-Rishitin", Chen, J.; Marx, J. N., Tetrahedron Lett., 1997, 38, 1889-1992.
"Measurement of Carbonyl Compounds as the 2,4-Dinitrophenylhydrazonate Anion. Reaction Mechanism and an Automated Measurement System.", Dasgupta, P, K.; Zhang, G.; Schulze, S.; Marx, J. N., Anal. Chem., 1994, 66, 1965-1970.
"Acid-Catalyzed Rearrangements of 4-Methyl-4-Cyanocyclohexadienone", Marx, J. N.; Zuerker, Hahn, Y. S. P., Tetrahedron Lett., 1991, 1921-1924.