ORGANIC CHEMISTRY - SYNTHESIS - CALIXNAPHTHALENES-ALKALOIDS
REGRETFULLY, DR. GEORGHIOU DOES NOT HAVE FUNDING FOR ANY POSTDOCTORAL POSITIONS AT PRESENT.
Calix[n]arenes (n=4-8) have generated much scientific and industrial interest because their structures enable them to act as "molecular baskets" towards neutral organic or ionic "guests". Recently, for example calixarenes have even been used to selectively complex with fullerenes, and have also been used as building blocks towards larger and more complex molecules.
In 1993 we reported the first synthesis of a new class of molecules that are closely related to calixarenes but are derived from 1-naphthol, the naphthalene analogue of phenol. These "calixnaphthalenes" possess larger cavities than the corresponding calixarenes and are also chiral due to the lack of symmetry inherent in the naphthalene units. Such properties can have important applications such as for example, being able to selectively bond with other molecules that have specific molecular structures or architectures. In this regard these molecules could be compared simplistically with enzymes. New molecules whose architecture can be controlled are desirable since no single type of molecular structure can provide a basis for the mimicry of all types of enzyme behavior. In order to achieve the objectives of molecular or ionic recognition/complexation, it is first necessary to develop synthetically useful routes to these compounds. My research group is currently involved in developing general synthetically useful routes to these compounds and other related cyclic molecules. For a very recent review of the compounds which we have synthesized and studied see the Account which was published in SYNLETT, 879-891, (2005).
Another research project that we have been involved in during the past two years is the development of new synthetic approaches towards the bisbenzylisoquinoline alkaloids. Our enantioselective total synthesis of Tejedine was published in Organic Lett., 4, 2675-2678, (2002).
Recent Publications: (click on link to access titles and journal pages)
macrocyclic container molecules." Completion date: September 2006.- Ph.D. Student –"Synthesis and properties of naphthalene-ring containing
calixarene derivatives and their optical properties." Expected completion date: December 2006.- Ph.D. Student –"Synthesis of narrow-rim-functionalized
- Ph.D. Student –"Synthesis of calixsalene derivatives and other calixnaphthalene-ring dendrimers and their chemical and properties." (with Prof. C. R. Jablonski). Expected completion date: December 2007.
enantioselective total synthesis of the bisbenzyltetrahydroisoquinoline alkaloid (-)cycleanine." Expected completion date: December 2008.- Ph.D. Student –"Continuing synthetic studies towards an
RECENT FORMER STUDENTS
Ningzhang Zhou - M. Sc. (2004) –"Further studies towards enantioselective total synthesis of the bisbenzyltetrahydroisoquinoline alkaloid (-) cycleanine". Mr. Zhou is currently pursuing his Ph.D. studies with Prof. Y. Zhao in the Dept. of Chemistry, M.U.N.
Giddings - M. Sc. (2003) –"An
examination of the synthesis and complexation
properties of selected macrocyclic compounds". Ms. Giddings is with Biovectra DCL, in Charlottetown, P.E.I.,
Cui - M.Sc. (2003) -"Progress
towards enantioselective total synthesis of the bisbenzyltetrahydroisoquinoline alkaloid(-)
cycleanine". Mr. Cui is at Boehringer-Ingelheim
Pharmaceuticals, Inc., Ridgefield, CT,
Mark S. Ralph - M.Sc. (2001)
–"Investigations into the asymmetric synthesis and biological
activities of some bisbenzyltetrahydroisoquinoline
Mr. Ralph is at Boehringer-Ingelheim
Pharmaceuticals, Inc., Ridgefield, CT,
Dr. You-Chou Wang - Postdoctoral Fellow (1999-2001) Dr. Wang is now Research Scientist at Wyeth . Synthesis of benzylisoqinolines.
- Ph.D. (2001) –"Complexation properties of calixnaphthalenes and related compounds". Dr. Mizyed is presently Assistant Professor, Chemistry Department, Yarmouk University, Irbid, Jordan.
- Ph.D. (2001) -"Deep molecular baskets: Convergent syntheses of calixnaphthalenes via directed ortho-metalation
and Suzuki-Miyaura coupling reactions": Dr. Chowdhury is Research Scientist at Xenon Pharmaceuticals,
Dr. Muhammad Ashram - PhD (1997)
- "Synthesis of calixnaphthalenes and their
properties": Dr. Ashram is presently Associate Professor, Chemistry
Department, Mu'Tah University, Al Karak,
Dr. Zhaopeng Li - PhD (1996) - "Synthesis and properties of calixnaphthalenes": Dr. Li was formerly Research Chemist at Witco Inc.,
Dr. Yi Ren - M.Sc (1992), Ph.D. (1997,
Dr. Jimmy (C.-K.) Ho - M.Sc
(1989), Ph.D. (1993,
Philip A. Blagden
- M.Sc (Toxicology) (1993) -
"Characterization and Evaluation of the Microsuspension
Procedure of the Salmonella typhimurium
Mutagenicity Assay with Application to PM10
Collected in Indoor Environments": Phil is now with Environment
Last modified August 26, 2006 by Prof. Paris Georghiou, Department of Chemistry, Memorial University of Newfoundland .