Philip LeQuesne

Emeritus Faculty

312 Hurtig Hall
Tel: 617.373.2858
Fax: 617.373.8795
p.lequesne@neu.edu

Organic Chemistry

Education:

1964 Ph.D., University of Auckland, Auckland, New Zealand
1961 M.Sc., University of Auckland
1960 B.Sc., University of Auckland

Research Interests

Prof. Le Quesne pursues research in the chemistry of natural products, naturally occurring organic molecules having MW between 150 and 1500, often with intricate structures. They are used for chemical communication: within a living organism they are hormones, and between different organisms they are pheromones. The work is dedicated to the isolation, structure determination, and synthesis of these biologically significant compounds, especially secondary metabolites (alkaloids, terpenoids, steroids, peptides) obtained from living organisms and possessing interesting physiological properties.

The main sources of research leads are folk medicine (ethnobotany), physiology (biological activity or toxicity), screening of organism extracts (e.g., for anticancer activity) and ecology (plant-insect interactions).

The research encompasses isolation, structure determination, and synthesis, either biomimetic or total synthesis. Isolation and structure determination work includes extraction of natural materials, purification of secondary metabolites of interest, and structural identification using high field NMR spectroscopy and X-ray crystallography. In recent years Prof. Le Quesne’s group has synthesized a number of novel compounds that were isolated earlier from natural sources, and they are currently also engaged in studies of new synthetic methods applicable to heterocyclic systems, especially pyrroles and indoles. Research is also underway in medicinal chemistry, particularly the development of analogues of natural wound-healing compounds.

Selected Publications

1. C.E.F.Rickard, P.W. Le Quesne, “Regio- and Stereo-selectivity in Metal Hydride Reductions of the Diels-Alder Adduct of Ergosteryl Acetate and Maleic Anhydride,” J. Org. Chem. 63: 1736 (1998).

2. Y. Dong, N. N. Pai, S. L. Ablaza, S.-X. Yu, S. Bolvig, D. A. Forsyth, P.W. Le Quesne, “Quararibea Metabolites. 4. Total Synthesis and Conformational Studies of (+)-Funebrine and (+)-Funebral,” J. Org. Chem. 64: 2657-2666 (1999).

3. P. W. Le Quesne, T. A. Blythe, Y. Dong, “Pyrrole Alkaloids and Related Compounds,” Alkaloids: Chemical and Biological Perspectives, Ed. by S.W. Pelletier, Vol. 13, Pergamon, Chapter 3 (1999).