Boss Keck Gary E. Keck
Professor
Department of Chemistry, U of U
Salt Lake City, UT 84112
Phone : (801) 581 - 7055
Fax: (801) 585 - 0024
E-Mail : keck@chemistry.utah.edu

Field of Interest : Organic Chemistry

Education

Table of Contents

Research Interests

(Links to keywords indicated in the text for this section are collected at the end.)

Research in our group focuses heavily on the total synthesis of natural products, particularly those with desirable biological activity of some sort. Structures currently of interest to us include rhizoxin, a promising antitumor agent, epothilone, also an antitumor agent, the antitumor alkaloid pancratastatin and related materials, pironetin, a very potent immunosuppressive agent, the unusually complex marine natural product swinholide, a very cytotoxic macrodiolide, and the bryostatins.

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. Use of chiral Lewis acid catalysts permits 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 some of 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 not traditionally considered as synthetic organic chemistry, 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....the exact synthetic reconstruction of a given naturally occurring structure.... makes such research both intellectually fulfilling and emotionally exciting.

Unfortunately, I cannot put details of current work up here. Tell you what though...grab a drink and some popcorn and come take a look at some of the transformations that we have developed. This should give you at least some idea of the kind of things of interest to us. We have these linked here as "Reactions". We will be adding new things, so check back.
| Structures | Synthesis | Reactions | Chiral Lewis Acids | Publications |

Short Biography

I was born May 21, 1949 to parents Ross and Elizabeth in Knoxville, Tennessee. The Kecks have been in eastern Tennessee for a very long time, and it is a very common name there. Thus I come from a long line of "hill people", and I am rather proud of my ancestry. I was the first of our particular family to be born in a hospital. I recall seeing two photo's of my dad and his siblings taken in front of my grandfathers home. The first was taken as he was going off to Europe in WWII. The second was taken upon his return, and there is one very noticeable difference...brand new power lines running alongside the dirt road in front of the house. (My dad served as a tail-turret gunner on a B-17. Interestingly, he survived the war with only minor injuries, only to crash in the Alps three days after the fighting had ceased. Obviously, he survived that also.)

My parents moved to Ohio when I was six, so that is where I grew up. I lived in Waterville and attended Anthony Wayne High School. I did my BS work at BGSU, majoring in chemistry and physics, and was lucky enough to be a participant in a summer research program at Argonne National Labs the summer following my junior year. There I worked with Lou Kaplan and Ken Wilzbach on photochemistry, and liked it so much that I decided to do my PhD in that area. That took me to Wisconsin, where I worked with Professor Howard Zimmerman. It was an exciting time to be at Wisconsin, and in the Zimmerman group. However, I found that I enjoyed the synthetic aspects of my research more than the physical end, and that took me to a postdoctoral position with Professor E. J. Corey at Harvard University. Again, I seemed to be in the right place at the right time! It was an especially exciting time to be in the Corey group, with syntheses of Maytansine, erythronolide, gibberelic acid, picrotoxinin, and many others all well underway. Some of my contemporaries there were Rick Danheiser, Homer Pierce, Dale Boger, KC Nicolaou, Alan Kozikowski, Jan Smith, Marcus Tius, David Floyd, Lee Weigel, JL Gras, and Larry Blaczak, to name just a few.

I came to Utah in 1977 to start my own group, and three students joined that year...Robb Webb, David Nickell, and John Yates. My group now is typically 10-12 people. On the personal side, I enjoy hunting and fishing, the shooting sports, good dogs, computing (although I am no expert) and music...primarily country and what would now be termed...*heavy sigh here*..."classic rock". Some favorites would include Merle Haggard, Hal Ketchum, George Strait, and Stevie Nicks. Amongst my prized possessions I would have to list a 76 LandCruiser named Merle and my Golden Retrievers "Jessie James" and "Dylan".

Please step on over to the Keck Group Homepage...all the good stuff is over there. :)

This Web page maintained by "Boss" Keck: keck@chemistry.chem.utah.edu

Back to Table of Contents