Professor (b. 1949)
B.S., Bowling Green State University, 1971
Ph.D., University of Wisconsin, Madison, 1975
Postdoctoral, Harvard University, 1975
Phone: (801) 581-7055

keck@chem.utah.edu

Awards and Activities
Alfred P. Sloan Fellow, 1981-85

Research Interests 
Research in our group focuses heavily on the total synthesis of natural products, particularly those with desirable biological activity of some sort. Representative of the structures currently of interest to us are the cytotoxic macrodiolide swinholide (1), and bryostatin 1 (2), a complex macrolide that is showing exciting activity in clinical trials against a variety of human cancers.

Closely related to our natural products work is our research on new synthetic methods, that is, the design of useful new organic reactions for applications in our total synthesis efforts. Often these evolve in a very natural way, in response to specific problems encountered in a synthesis or in response to certain key structural features presented by a given target.

Much of our current research in this area is focused upon the development of methodology for use in the synthesis of complex materials where stereochemistry is of primary concern. Many of these reaction types involve the complexation and activation of a carbonyl compound by a Lewis acid of some sort, and studies of both complexation phenomena and reaction mechanisms via variable temperature multinuclear NMR spectroscopy have proven valuable in developing and refining such reactions. A current emphasis is on the use of chiral Lewis acid catalysts that we have developed to carry out transformations that yield predominantly one enantiomer of product from achiral reactants. The design of synthetically useful reactions involving radical intermediates represents another long-standing interest in our research group, and these have been applied in several syntheses as well.

Hence, due to our blend of total synthesis with methods development, my students are exposed to, and work in, a wide variety of areas, from theory and reaction mechanisms to conformational analysis, spectroscopy, and computational chemistry. Natural products synthesis is thus, in our view, an excellent vehicle for the development of the intellectual acumen and experimental techniques necessary for success in any area of organic research.

Finally, it should be noted that this type of research is very demanding yet equally rewarding. It is difficult to describe the satisfaction of seeing the new reactions one develops successfully applied to the synthesis of an important natural product, or the excitement at the end of a synthesis as the final spectral and chromatographic comparisons of natural and synthetic material are completed. The strange dichotomy between the infinite number of possible approaches to a given complex structure and the bottom line of such investigations-exact synthetic reconstruction of a given naturally occurring structure-makes such research both intellectually fulfilling and emotionally exciting.

Selected Publications 

• "Synthetic Studies toward the Bryostatins: A Substrate Controlled Approach to the A-Ring", G. E. Keck, D.  S. Welch, and P.  K. Vivian, Org. Lett. 2006, 8, 3667-3670.
• "Total Synthesis of (+)-Dactylolide", C. C. Sanchez  and G. E. Keck, Org. Lett. 2005, 7, 3053-3056.
• "Enantio- and Diastereoselective Additions to Aldehydes Using the Bifunctional Reagent 2-(Chloromethyl)-3-(tributylstannyl)propene: Application to a Synthesis of the C16-C27 segment of Bryostatin 1", G. E. Keck,  T. Yu, and M. D. McLaws, J. Org. Chem. 2005, 70, 2543-2550.
•  "Synthetic Studies on the Bryostatins: Synthetic Routes to Analogues Containing the Tricyclic Macrolactone Core", G. E. Keck and A. P. Truong, Org. Lett. 2005, 7, 2153-2156.
• "Pyran Annulation: Asymmetric Synthesis of 2,6-Disubstituted-4-methylene Tetrahydropyrans", G. E. Keck, J. A. Covel, T. Schiff, and T. Yu, Org. Lett. 2002, 4, 1189-1192.
• "Intramolecular Baylis-Hillman and Morita Reactions Using Unsaturated Thiol Ester Substrates Containing Enolizable Aldehydes", G. E. Keck and D. P. Welch, Org. Lett. 2002, 4, 3687-3690.
• "Asymmetric Total Synthesis of Rhizoxin D", G. E. Keck, C. A. Wager, T. T. Wager, K. A. Savin, J. A. Covel, M. D. McLaws, D. Krishnamurthy, and V. J. Cee, Angew. Chem. Int. Ed. (English)  2001, 40, 231-234
• "Total Synthesis of the Immunosuppressant (-)-Pironetin (PA48153C)", G. E. Keck, C. E. Knutson, and S. A. Wiles, Org. Lett. 2001, 3, 707-710.
• "The First Directed Reduction of b-Alkoxy Ketones to Anti-1, 3-Diol Monoethers; Identification of Spectator and Director Alkoxy Groups", G. E. Keck and C. A. Wager, Org. Lett. 2000, 2, 2307-2309.
• "Total Syntheses of (-)-Lycoricidine, (+)-Lycoricidine, and (+)-Narciclasine via 6-exo Cyclizations of Substituted Vinyl Radicals with Oxime Ethers", G. E. Keck, T. T. Wager, and J. F. D. Rodriquez, J. Am. Chem. Soc. 1999, 121, 5176-5190.
• "Catalytic Asymmetric Allylation Reactions Using BITIP Catalysis and 2-Substituted Allylstannanes as Surrogates for b-Keto Ester Dianions", G. E. Keck and T. Yu, Org. Lett. 1999, 2, 289-292.
• "A Second-Generation Radical-Based Synthesis of (+)-7-Deoxypancratistatin", G. E. Keck, T. T. Wager, and S. F. McHardy, J. Org. Chem. 1998, 63, 9164-9165.