David B. Berkowitz is a native of Chicago, and graduated Phi Beta Kappa in Chemistry from the University of Chicago. He then pursued graduate studies at Harvard University, moving with his advisor, Steven Benner, to the ETH-Zürich, in the course of his doctoral research. Dr. Berkowitz returned to the U.S. to serve as a Merck Postdoctoral Fellow with Samuel Danishefsky at Yale. In 1991, he took a faculty position at the University of Nebraska, where he is currently Professor of Chemistry, and holds membership in the Centers for Biotechnology, Energy Sciences, Toxicology and Cancer (Eppley Institute – Omaha). Berkowitz has been recognized as a Fellow of the Alfred P. Sloan Foundation (1997-01) and of the Japan Society for the Promotion of Science (2008-09). His honoraria include Visiting Professorships at the Université de Rouen (Normandy, France, 2005) and the Max Planck Institute (Dortmund, Germany, 2006).
The Berkowitz group has interests in the areas of synthetic organic chemistry, asymmetric and combinatorial catalysis, medicinal chemistry, biofuel stream-based synthesis, and mechanistic enzymology. More specifically, the group is known for (i) methodology development and bioorganic study of “teflon phosphates,” – i.e. fluorinated phosphonate mimics of biological phosphates, particularly phospho-sugars and amino acids. (ii) The group continues to pursue the asymmetric total synthesis of lignans of the podophyllum class, as potential anti-neoplastic agents. (iii) The Berkowitz research team has a long-standing interest in unnatural amino acids, particularly those of the quaternary, β,γ-unsaturated variety, as inactivators of specific vitamin B6-dependent enzymes. (iv) Most recently, the group has exploited enzymes as both chiral reagents and chiral sensors in asymmetric and combinatorial catalysis.
This talk will focus on two topics that cut in opposite directions
at this interface. In one sense, the former topic speaks to drug
discovery, and the latter, to process chemistry. On the one hand,
we will discuss how an understanding of the details of enzyme
mechanism can be exploited to design new “mechanism-based”
enzyme inactivators. In this regard, fluorine plays an integral
role in both trigger actuation, in the target active site, and as
a “spectroscopic beacon” providing useful information,
by 19F NMR, on how the inhibitor partitions in that active site.
Methods for the stereocontrolled synthesis of quaternary, α-branched
amino acids will be discussed, as will target enzyme purification,
and both kinetic and spectroscopic examination of enzyme inactivation.
On the other hand, the Berkowitz group has developed a program in
combinatorial catalysis that revolves around the use of enzymes as
analytical tools to facilitate the catalyst screening process. We
term this approach In Situ Enzymatic Screening (ISES). In such
endeavors, issues to be addressed include information content of
the screen, sensitivity, convenience and throughput. As ISES screens
are developed, this is done in the context of catalyst/ligand
development for transformations of real synthetic interest to the
group. Discussed will be combinatorial catalytic approaches to
transition metal-based allylic amination, Co(III)-salen based
hydrolytic kinetic resolution, and a new halometalation/carbocyclization
route to fused, sesquiterpene lactone natural product cores.
Professor Jeffrey Bode
University of Pennsylvania
Jeffrey Bode was born in southern California and grew up in California and New Mexico. He received his B.S. in Chemistry at Trinity University, where he worked with Prof. Michael P. Doyle. He received his Dok. Nat. Sci. degree in 2001 from the California Institute of Technology and the Swiss Federal Institute of Technology (ETH) in Zurich, Switzerland under the direction of Prof. Erick M. Carreira. From 2001–2003, he was JSPS postdoctoral fellow at the Tokyo Institute of Technology in the laboratories of Prof. Keisuke Suzuki. In August 2003, Jeffrey returned to California as an Assistant Professor of Chemistry and Biochemistry at the University of California, Santa Barbara and in September 2007 moved to the University of Pennsylvania where he is Associate Professor of Chemistry. Research in his group includes the development of new reactions for asymmetric synthesis and chemoselective ligation and the application of these methods to the synthesis of structures ranging from small, bioactive molecules to modified proteins to new biomaterials. His research and teaching have been recognized by awards including a Camille and Henry Dreyfus New Faculty Award, a National Science Foundation CAREER Award, a Beckman Young Investigator Award, a Research Corporation Cottrell Scholar Award, an Alfred P. Sloan Foundation Fellowship, and a David and Lucille Packard Foundation Fellowship as well as by young investigator award from Amgen, AstraZeneca, Bristol-Myers Squibb, Eli Lilly, and Roche. In 2008, he was selected as an Arthur C. Cope Scholar by the American Chemical Society and listed as one of Discover Magazine’s “Top 50 Brains in Science”.
Amide bond formation is one of the most widely used chemical reactions and constitutes the core of modern peptide synthesis. Despite its importance, there is but one general reaction manifold for the synthesis of amide bonds. Although extremely powerful, this paradigm for amide formation has inherent limitations that not only prohibit the efficient synthesis of larger structures including proteins and therapeutic peptides but also result in the generation of large amounts of chemical waste. In addressing these issues, we have developed two conceptually novel approaches to amide bond formation. One of these methods allows chemoselective coupling of completely unprotected molecules without the need for reagents, protecting groups, or starting materials. The second approach makes possible waste-free, catalytic amidations from simple starting materials via a novel N-heterocyclic carbene catalyzed pathway that has far reaching implications for the development of new synthetic methods, including enantioselective carbon–carbon bond forming reactions.
11:00 – Coffee Break
Professor Bruce H. Lipshutz
University of California, Santa Barbara
Bruce H. Lipshutz received his B.A. in 1973 from SUNY Binghamton and a Ph.D. in 1977 from Yale University under the direction of Harry H. Wasserman. In 1977 he moved to Harvard University as a postdoctoral research fellow in the laboratories of E. J. Corey. He joined the faculty of the University of California, Santa Barbara in 1979 and became a full professor at UCSB in 1987. He has received numerous honors and awards including the ACS Junior Faculty Research Award (1981-83), Alfred P. Sloan Foundation Fellow (1984-88), the Harold J. Plous Memorial Teaching Award, UCSB, (1984), Camille and Henry Dreyfus Teacher-Scholar (1984-89), the American Chemical Society Arthur C. Cope Scholar Award (1997), UCSB Foundation Distinguished Faculty Teaching Award (2002), and the Solvias Ligand Prize (2003).
Much of his career has been focused on developing new reagents and technologies that have broad appeal in the synthetic community, many of which are now, or will soon be, commercially available (e.g., SEM-Cl, “Higher Order Cuprates”, “Cuprate-in-a-Bottle”, DCAD, “Copper Hydride-in-a-Bottle”, Ni/C, Cu/C, PTS, etc.). The group's efforts have now turned in part to “green chemistry”. Thus, an ongoing mix of methods in heterogeneous catalysis, including newly developed mixed metal-supported cross-coupling reagents, and homogeneous catalysis. The latter includes recent contributions in micellar catalysis, with an accent on development of “designer surfactants”. Also being actively pursued are projects in total or partial synthesis of biaryls that possess axial chirality (e.g., the A-B biaryl section of vancomycin, and the antimalarial korupensamines), and syntheses associated with, and analogs derived from, coenzyme Q10 (e.g., total synthesis of piericidin A1).
This discussion will focus on new, alternative technologies for efficiently making bonds via transition metal-catalyzed couplings, with two important criteria: (1) water is the only medium for these reactions, and (2) they can be run at room temperature. Thus, the overriding theme will be to “get organic solvents out of organic reactions.”
The methodologies developed take advantage of micellar catalysis, which allows for water-insoluble substrates to be coupled under homogeneous conditions, in water at rt. Two “designer” surfactants that form nanoreactors in water will be presented: PTS and PQS.
Although several “name” reactions have already been described using this approach (olefin metathesis, Heck, Suzuki-Miyaura and Sonogashira), this presentation will focus on unpublished work. Thus, newly devised procedures for carrying out aminations of aryl halides, allylic alcohols, and allylic ethers, in water at rt will be presented. Lastly, the potential for this approach to be applied to reactive metal chemistry will be disclosed by a discussion of Negishi couplings of organozinc halides…in water. Really.
12:15 – Lunch Break
Professor John L. Wood
Colorado State University
“Synthetic Studies of Oxindole-Containing Natural Products”
John L. Wood was born on December 4, 1961 in Keokuk Iowa. He received a B.A. degree from the University of Colorado in 1985 and a Ph.D. from the University of Pennsylvania in 1991 under the direction of Amos B. Smith, III. In 1991 he moved to Harvard University as an American Cancer Society postdoctoral fellow and continued studying natural products synthesis in the laboratories of Stuart Schreiber. He joined the faculty at Yale University in 1993 as an Assistant Professor and was promoted to Full Professor in 1998. In 2006, Professor Wood joined the faculty at Colorado State University as the Albert I. Meyers Professor of Chemistry. Professor Wood received a Camille and Henry Dreyfus New Faculty Award in 1993, an American Cancer Society Junior Faculty Award in 1994, an NSF CAREER award in 1996, an Eli Lilly Young Faculty Award in 1996, a Glaxo-Wellcome Chemistry Scholar Award in 1996, and a Bristol-Myers Squibb Research Award in 1997. He was the Parke-Davis Distinguished Michigan Lecturer in 1997 and received a Novartis Chemistry Lectureship and an Alfred P. Sloan Fellowship in 1997. He served as the guest editor for the Tetrahedron Symposium in Print on Synthetic Methods V and as a visiting Professor at the University of Auckland. In 1998 Professor Wood was the recipient of research awards from the Bristol-Myers Squibb Foundation, the Yamanouchi USA foundation, and received the Zeneca Excellence in Chemistry Award. In 2000 Professor Wood received a Merck Faculty Award and in 2001 he was awarded The Kitasato Intistute’s Microbial Chemistry Medal. He was invited to the executive board of editors for Tetrahedron publications in 2002 and is currently a co-editor for Tetrahedron Letters.
Professor Wood was named as a 2004 Cope Scholar by the American Chemical Society and as a Fellow to the Japanese Society for the Promotion of Science in 2008.
Recent efforts in our laboratories have focused on the synthesis of several oxindole-containing natural products. The evolution of synthetic strategies directed toward the welwitindolinones and citrinadins will be discussed.
Professor Robert H. Grubbs
California Institute of Technology
Born February 27, 1942, near Possum Trot, Kentucky. B.S., Chemistry,
University of Florida, Gainesville, Florida, 1963; M.S., Merle
Battiste, 1965. Ph.D., Ronald Breslow, Chemistry, Columbia University,
New York, New York, 1968. NIH Postdoctoral Fellow, James P. Collman,
Chemistry, Stanford University, 1968-69.
Dr. Robert H. Grubbs is currently the Victor and Elizabeth Atkins
Professor of Chemistry at the California Institute of Technology,
Pasadena, California, USA, where he has been a faculty member since
1978. Before moving to Caltech, he was at Michigan State University
from 1969 to 1978 achieving the rank of Associate Professor.
The research group of Grubbs is involved in the design, synthesis,
and mechanistic studies of complexes that catalyze basic organic
transformations. The major focus of the group over the past few
years has been on the olefin metathesis reaction. To optimize the
utility of this reaction, new catalysts have been developed that
are extremely tolerant of organic functional groups. Due to their
high-activity, functional group tolerance, and ease of use, these
ruthenium based catalysts have found wide applications in organic
and polymer synthesis. He has 475+ publications and 100+ patents
based on his research.
Professor Grubbs awards have included Alfred P. Sloan Fellow
(1974-76), Camille and Henry Dreyfus Teacher-Scholar Award (1975-78),
Alexander von Humboldt Fellowship (1975), ACS National Award in
Organometallic Chemistry (1988), Arthur C. Cope Scholar Award (1990),
ACS Award in Polymer Chemistry (1995), Nagoya Medal of Organic
Chemistry (1997), Fluka Reagent of the Year (1998), Mack Memorial
Award (1999), Benjamin Franklin Medal in Chemistry (2000), ACS
Herman F. Mark Polymer Chemistry Award (2000), ACS Herbert C. Brown
Award for Creative Research in Synthetic Methods (2001), ACS Arthur
C. Cope Award (2002), ACS Award for Creative Research in Homogeneous
or Heterogeneous Catalysis (2003), Richard C. Tolman Medal (Southern
California Section ACS - 2003), ACS Tetrahedron Prize for Creativity
in Organic Chemistry (2003), Pauling Award Medal (2003), Bristol-Myers
Squibb Distinguished Achievement Award in Organic Synthesis (2004),
Kirkwood Medal (2005) (New Haven Section, ACS), Paul Karrer Gold
Medallion (2005) (University of Zurich),
August-wilhelm-von-Hofmann-Denkmunze (2005) (German Chemical Society),
Nobel Prize in Chemistry (2005), Havinga Medal (2006) (Leiden
University), Golden Plate Award (2006) (Academy of Achievement),
and Tetrahedron Most Cited Paper 2003-2006 Award (“Olefin
Metathesis”), Tetrahedron Letters Most Cited Paper 2005-2008
Award (“A Neutral, Water-Soluble Olefin Metathesis Catalyst
Based on an N-Heterocyclic Carbene Ligand”), ACS Award for
Creative Invention (2009). He was elected to the National Academy
of Sciences in 1989, Fellow of the American Academy of Arts and
Sciences in 1994, and the Honorary Fellowship of the Royal Society
of Chemistry in 2006.
4:00 – Closing Remarks
The Symposium will include a continental breakfast,
luncheon, and refreshment break.
There is no fee for this event, thanks to the generosity of our sponsor,
sanofi-aventis. The Symposium will include lunch and coffee break.
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