Background:
- NIH Postdoctoral Fellow, Harvard University, 1976-78
- Alfred P. Sloan Fellow, 1983
- Merck Faculty Development Award, 1996
- Indiana University Teaching Excellence Recognition Award, 2000
- Tracy M. Sonneborn Award, 2002
The research efforts of our group involve synthetic organic chemistry in its very broadest sense. We undertake fundamental studies in the chemistry of recently discovered, biologically active natural products, such as terpenes, alkaloids, and antibiotics, which are structurally unique and thus far unexplored.
Generally, our efforts are focused on the preparation of complex substances of pharmacological significance. Present studies are directed toward new agents for treatment of cardiovascular disorders and neoplastic diseases, as well as new antibiotics.
These efforts are designed to produce new synthetic methodology, expanding the basic body of knowledge for designing organic syntheses and understanding chemical reactions to allow formation of complex arrangements of stereochemistry and polyfunctionality.
Previous successes have led to methods for the stereocontrolled formation of highly substituted tetrahydrofurans and related heterocyclic systems. New techniques for the preparation of medium-sized carbocyclic rings, and the transannular chemistry of such systems, have fueled our interest in terpenoids of marine origin. Enantioselective methodology toward the development of organometallic reagents has continued to be a primary objective, particularly for synthesis of complex acyclic or macrocyclic antibiotics. In our laboratories, chemical discovery is driven with the anticipated, and sometimes unanticipated, challenges presented by the unique molecular architecture of the targeted natural products, such as those in the accompanying illustrations. The finest examples of our achievements are intended to express the art of organic chemistry, as well as the basis for new fundamental information of chemical selectivity and synthetic strategy.
We use advanced nuclear magnetic resonance techniques and mass spectrometry on a daily basis, as well as flash and liquid chromatography and X-ray crystallographic analysis. Graduate students conduct research on well-defined, individual projects involving a wide range of reactions and types of compounds. This provides a very broad base of experiences to enhance the knowledge and creativity of the future scientist.
Selected Publications:
"Total synthesis of ( )-breynolide," with P. A. Jass, H.-L. A. Tse, and R. D. Gaston. J. Am. Chem. Soc., 112, 4552 (1990).
"Synthesis strategies for marine diterpenes. Total synthesis of the clavularanes," with P. J. Coleman and S. S. Henry. J. Am. Chem. Soc., 115, 11654 (1993).
"Total synthesis of myxovirescin A1," with J. Li. Tetrahedron Lett., 35, 5113 (1994).
"Total synthesis of (-)-stemoamide," with J. P. Reddy and G. S. Amato. Tetrahedron Lett., 35, 6417 (1994).
"Studies on the dolabellanes: stereoselective transannular cyclizations of dolabelladiene macrocycles," with P. J. Coleman. Tetrahedron Lett., 36, 39 (1995).
"Total synthesis of rhizoxin D," with K. M. Werner and B. Feng. Tetrahedron Lett., 38, 6825 (1997).
"Studies of zoanthamine alkaloids. Enantiocontrolled construction of the tetracyclic hemi-aminal core," with G. S. Cortez. Tetrahedron Lett., 39, 2675 (1998).
"Asymmetric allylation. An effective strategy for the convergent synthesis of highly functionalized homoallylic alcohols," with D. A. Brooks, K. G. Meyer, and M. P. Clark. Tetrahedron Lett., 39, 7251 (1998).
"Total synthesis of ( )-amphidinolide J," with W. S. Kissel. J. Am. Chem. Soc., 120, 11198 (1998).
"Regioselective ring metalation in [2,4]-bisoxazoles," with D. A. Brooks, K. G. Meyer, and M. Pagel. Tetrahedron Lett., 39, 8023 (1998).
"Studies of acyl nitrene insertions. A stereocontrolled route toward lankacidin antibiotics," with C. M. Rojas and S. L. Bogen. J. Org. Chem., 64, 736 (1999).
"The macrocyclic domain of phorboxazole A. A stereoselective synthesis of the C1-C32 macrolactone," with M. P. Clark. Tetrahedron Lett., 40, 2291 (1999).
"Total synthesis of (-)-hennoxazole A," with D. A. Brooks and M. A. Berliner. J. Am. Chem. Soc., 121, 4924 (1999).
"Palladium-induced cyclizations for the synthesis of cis-2,5-disubstituted-3-methylene-tetrahydrofurans: studies of the C7-C22 core of amphidinolide K," with K. G. Meyer. Org. Lett., 1, 1303 (1999).
"Total synthesis of (-)-amphidinolide P," with B. J. Myers and L. Mi. Org. Lett., 2, 945 (2000).
