awards
1998 ACS National Award Winners
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ollowing are vignettes of the winners of the American Chemical Society's new Herbert C. Brown Award for Creative Research in Synthetic Methods, the Arthur C Cope Award, and the Arthur C Cope Scholar Awards. The Brown Award will be presented at the ACS national meeting in Dallas. The Cope winners will receive their awards at the ACS national meeting in Boston dwring the Arthur C Cope Symposium, organized by the ACS Division of Organic Chemistry. The Cope Award recognizes and encourages excellence in organic chemistry. It consists of a medal, a personal cash prize of $25,000, and an unrestricted research grant of $150,000 to be assigned by the recipient to any university or nonprofit institution. Cope Scholar Awards consist of $5,000, a certificate, and an unrestricted research grant of $40,000. Each recipient Brown is required to deliver a lecture at the Arthur C. Cope Symposium. "In 1938, when I received my Ph.D. degree, I felt that organic chemistry was a relatively mature science, with essentially all of the important reactions and strucHerbert C. Brown Award tures known. There appeared to be little for Creative Research in new to be done except the working out of Synthetic Methods reaction mechanisms and the improvement of reaction products. I now recogSponsored by Aldrich Chemical Co., and nize that I was wrong. . . . I see no reason the Purdue Borane Research Fund for believing that the next 40 years will At the ACS Board of Directors meeting.at not be as fruitful as in the past." the society's fall 1997 national meeting, Brown was born in London in 1912 board members voted that the first recip- but immigrated to the U.S. He received ient of this new award should be its B.S. and Ph.D. degrees in chemistry from namesake, 1979 chemistry Nobel Laure- the University of Chicago in 1936 and ate and Purdue University Professor 1938, respectively. Following a year of postdoctoral work with M. S, Kharasch, Emeritus HERBERT C. BROWN. Brown is perhaps best known for his he was appointed to the staff of the Unicareer-long exploration of the role of bo- versity of Chicago as an instructor. In ron in organic chemistry. He discovered 1943, he moved to Wayne University that the simplest compound of boron and (now Wayne State) in Detroit, and in hydrogen—diborane—adds with remark- 1947, he became a professor of chemistry able ease to unsaturated organic mole- at Purdue University, West Lafayette, Ind., cules to give organoboranes. With or- where he is now Wetherill Research Proganoboranes now readily available for the fessor Emeritus. first time, he undertook to explore their Brown has published more than 1,200 chemistry—"a new continent in chemis- papers and he is currently coauthoring try," many observers have remarked. Oth- (with P. V. Ramachandran) a book entier colleagues say, "It may well be consid- tled "A General Asymmetric Synthesis via ered the most important synthetic accom- Chiral Organoboranes." During his caplishment of this century." reer, he has directed the work of 163 After receiving the Nobel Prize for his graduate students and 250 postdoctoral work on organoboranes, Brown wrote, researchers. 84 FEBRUARY 23, 1998 C&EN
Brown was elected to the National Academy of Sciences in 1957 and the American Academy of Arts & Sciences in 1966. Among numerous awards and honors he has received that span the global chemistry community are the Centenary Lecturer and Medalist of the Chemical Society, London (1955); the ACS Award for Creative Research in Organic Chemistry (I960); the National Medal of Science (1969); the Chemical Pioneer Award from the American Institute of Chemists (1975); ACS's Priestley Medal (1981); the Perkin Medal of the Society of Chemical Industry (1982); and the Chemical Sciences Award and Medal of the National Academy of Sciences (1987). He has also received Japan's highest decoration for a foreign scientist: Order of the Rising Sun, Gold and Silver Star (1989).
Arthur C. Cope Award SAMUEL J. DANISHEFSKY, director of the Laboratory for Bioorganic Chemistry at Memorial Sloan-Kettering Cancer Center, New York City, and professor of chemistry at Columbia University, has achievements in carbohydrate chemistry and biochemistry that stand "as a notable tour de force, combining synthetic expertise with mechanistic insight and a keen awareness of biological relevance," according to one colleague. Danishefsky, he adds, has helped change "the way organic chemists now carry out the synthesis of carbohydrates." Recent major contributions by Danishefsky's research group include a practical approach to the solid-phase synthesis
Danishefsky
of glycopeptides and the first use of poly mer-supported synthesis to construct a complex branched blood-group determi nant—the Lewis Y antigen, which is asso ciated with colon cancer. In addition, Danishefsky and coworkers recently reported the first total synthesis of a human breasttumor-associated antigen and its conjuga tion to a carrier protein—work that could aid development of a tumor vaccine. Danishefsky's interest in carbohydrate chemistry arose from his studies of organ ic synthesis. For example, his work on cyclocondensation reactions led to syntheses of pyranosides and higher-order monosac charides such as tunicamycin and neur aminic acid. "These syntheses," writes a colleague, "resulted in the elaboration of polyoxygenated structures bearing as many as eight contiguous hetero-substituted stereogenic centers in a few steps." Danishefsky also used the cyclocondensa tion strategy to synthesize zincophorin, an antibiotic, and 6-deoxyerythronolide B, the parent compound of the antibiotic erythromycin. In the past few years, Danishefsky's ma jor focus has been on the use of glycals as glycosyl donors and acceptors in the syn thesis of complex oligosaccharides and glycoconjugates. The glycal technique has provided the basis for the syntheses of a chitinase inhibitor (allosanadin), a phos phodiesterase inhibitor (KS-501), the sac charide portion of the antibiotic vancomy cin, and the saccharide domain of the principal enediyne antibiotics, among oth er structures. Danishefsky's group has also used gly cals to produce oligosaccharides such as the cell-adhesion ligand sialyl Lewis X, as well as nucleosides, gangliosides, and glycopeptides. Glycal technology opens a complete route to synthetic oligosac charides and associated structures.
Arthur C. Cope Scholar Awards GREGORY C. FU, assistant professor of chemistry at Massachusetts Institute of Technology, "has established a vigorous research program in organic chemistry," says one colleague, with work "charac terized by an elegance and creativity of design." Fu has made significant contributions to several areas of chemical synthesis. These achievements include developing new transformations of organotin re agents, exploring the chemistry of bora-
benzenes, and designing and synthesiz ing a new class of enantioselective nucleophilic catalysts. In his work with organotin com pounds, Fu has developed new stoichio metric and catalytic reactions of Bu3SnH. His accomplishments include the discov ery of a new pinacol coupling process as well as catalytic methods for effecting re ductive cyclizations and Barton-McCombie deoxygenations. In another area of research, Fu has de veloped efficient syntheses of borabenzene derivatives and has investigated their reactivity. He has begun to explore their application as chiral Lewis-acid cat alysts and as ligands for transition metals. Fu's work on enantioselective nucleophilic catalysts has resulted in the devel opment of a versatile new family of cata lysts, and he has achieved alcohol acylation reactions at the 99% enantiomeric excess level. "These systems have excel lent promise and represent a real break through in the general area of nucleophilic catalyst design," says a colleague. Fu received a B.S. degree in 1985 from MIT, where he carried out research in asymmetric Michael reactions with Joel M. Hawkins in the laboratory of K. Barry Sharpless. He went on to receive a Ph.D. degree from Harvard University in 1991. At Harvard, his thesis with David A. Evans focused on transition-metal-catalyzed hydroboration reactions. He then spent two years as a postdoctoral fellow at California Institute of Technology with Robert H. Grubbs, where he worked on the ringclosing olefin metathesis reaction. In 1993, Fu joined ΜΓΓ as an assistant professor, and in 1996 he was named Firmamich As sistant Professor of Chemistry. In addition to the Cope Scholar Award, Fu has received several other honors, in cluding a Camille Dreyfus Teacher-Scholar Award, an Alfred P. Sloan research fellow ship, a Cottrell Scholar Award, and a Na tional Science Foundation Young Investi gator Award.
ten a hybrid between inorganic and or ganic chemistry." He uses his discoveries in the chemistry of transition-metal com plexes to create new synthetic methods based on explorations of the mechanistic details of the individual organometallic reactions. Hartwig has developed practical palla dium-catalyzed methods for adding aryl groups to amines, alcohols, and ketones. His group has devised a general proce dure for forming carbon-nitrogen bonds that avoids the use of toxic tin reagents. He discovered the first general nitrogenhydrogen activation of primary amines, a reaction that generates an amido com plex involved in the catalytic arylation of amines. In addition, he has observed re ductive elimination to form carbon-nitro gen bonds in amines and carbon-sulfur bonds in sulfides—new fundamental re actions of organometallic compounds. In another area of research, Hartwig discovered a process that uses com pounds with a covalent bond between a transition metal and boron to convert alkanes to organoboranes, commonly used as synthetic intermediates. Hartwig received an A.B. degree in chemistry from Princeton University in 1986. He received a Ph.D. degree in chem istry at the University of California, Berke ley, where his research advisers were Rob ert G. Bergman and Richard A. Andersen. He worked with Stephen J. Lippard at Massachusetts Institute of Technology as an American Cancer Society postdoctoral associate, then joined Yale as assistant pro fessor of chemistry in 1992. Among other honors, Hartwig received a Camille & Henry Dreyfus Foundation New Faculty Award in 1992, a National Science Foundation Young Investigator Award in 1994, and a Camille Dreyfus Teacher-Scholar Award in 1997. He was awarded an Alfred P. Sloan Research Fel lowship in 1996.
AMIR H. HOVEYDA, professor of chem istry at Boston College, has been hailed Yale University associate professor of by colleagues as "the foremost synthetic chemistry JOHN F. HARTWIG is "without organic/organometallic chemist of his question the most promising young or- generation." ganometallic chemist of his age group," ac Hoveyda was a postdoctoral fellow at cording to one colleague. Another de Harvard University under David Evans and scribes Hartwig as "an outstanding scholar also spent a brief time as a member of the who has been able to make an impressive cancer group at Pfizer Central Research, impact in several new areas of transition- Groton, Conn. In June 1990, he moved to metal organic chemistry in only a few Boston College as an assistant professor, years by using his background in physical and his work as an independent research chemistry as a guide to the invention of er began. In the seven years since, "Hovey new reactions." da has shown a cunning ability to design Hartwig characterizes his work as "of new metal-based organic reactions, develFEBRUARY 23, 1998 C&EN 85
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op diastereoselective and enantioselective variants, and apply them in practical con texts," says a colleague. One of the themes of Hoveyda's re search has been the zirconium-catalyzed carbomagnesation of alkenes. He was the first to establish that such carbon-carbon bond-forming additions can be effected with good chemical yields. He also de fined the regioselectivity and diastereoselectivity of these reactions. He optimized diastereoselectivity by matching pairs of chiral nonracemic substrates and cata lysts. This effort led to a catalyst that is able to control absolute stereochemistry, allowing the conversion of achiral al kenes to chiral addition products in high enantiomeric excesses. With colleague Marc L. Snapper, Ho veyda used combinatorial chemistry to prepare, screen, and optimize a variety of peptidic ligands, which led to dipeptide-titanium catalysts. The complexes made it possible to perform the first en antioselective synthesis of a β-cyanohydrin (C&EN, Nov. 4, 1996, page 37). "His new reaction development is often accompanied by extensive and detailed experiments designed to elucidate the subtle inner workings of a system. That is Hoveyda's strength," said one colleague. It was this strength and strategy that led to the total synthesis of Sch385l6, an antifun gal agent, in 1995. He used a wide range of catalytic reactions, developed in his own laboratories and others, to complete this synthesis, which demonstrated for the first time that catalytic ring-closing me tathesis can be used to construct complex macrocyclic structures efficiently. Hovey da hopes his research efforts will develop efficient catalytic processes for selective and economical preparations of chiral molecules. Hoveyda, who has published approxi mately 40 papers, won the National Sci 86 FEBRUARY 23, 1998 C&EN
Hoveyda
ence Foundation National Young Investi gator Award in 1992, the Pfizer Research Award in Synthetic Organic Chemistry in 1993, and a Camille Dreyfus TeacherScholar Award in 1994, among numerous other honors. Hoveyda received a B.A. degree from Columbia University in 1981 and a Ph.D. degree in organic chemistry under Stuart Schreiber from Yale University in 1986. GARY A. MOLANDER, professor of chemistry and biochemistry at the Uni versity of Colorado, Boulder, has made a career of developing efficient methods for the synthesis of organic molecules. Throughout his years as a researcher, Molander has focused on four areas: the development of samarium(II) iodide (SmQ as a reagent for organic synthesis, the development of group-3 organometallics and organolanthanides and group-4 cationic complexes as catalysts for selec tive organic transformations, the invention of annulative approaches to the synthesis of seven- and eight-membered carbocycles, and the development of new strate gies for remote asymmetric induction. In addition, his group has been active in se quencing one-pot organic reactions to im prove synthetic efficiency. In his research on the chemistry of Sml2—probably his best known work— his group has studied C-C bond-forming processes such as the intramolecular Barbier reaction, the intramolecular Reformatsky reaction, pinacol couplings, ketyl-olefin couplings, nucleophilic acyl substitution reactions, cyclopropanation, and intramolecular conjugate addition reactions. He also has studied reductions of ke tones, aldehydes, and oc-heteroatomsubstituted ketones. "In addition to the practical value of his research," says a colleague, "it has served to waken the
Molander
organic chemical community to the enormous potential of lanthanides as re agents and catalysts for selective organic transformations. " Molander received a B.S. degree in chemistry from Iowa State University, Ames, in 1975 and a Ph.D. degree in chemistry from Purdue University, West Lafayette, Ind., in 1979. He spent several months as a postdoctoral fellow at Purdue, followed by nearly two years as a National Institutes of Health postdoctoral fellow at the University of Wisconsin, Madison, be fore joining the Colorado faculty as an as sistant professor in 1981. In 1988, he be came an associate professor, and in 1990 he was promoted to professor. Molander has received several awards and honors throughout his career, in cluding an Alfred P. Sloan Foundation Fellowship, the American Cyanamid Aca demic Award, and an Eastman-Kodak Fel lowship. He has been a visiting professor at universities in France and Germany. He also was associate chairman of the department of chemistry and biochemis try at Colorado from 1992 to 1995. JAMES S. NOWICK, associate professor at the University of California, Irvine, is recognized for his work with peptidomimetic compounds and molecular recog nition. Nowick and his team have devel oped "artificial β-sheets" as chemical model systems with which to study pro tein β-sheets. An enhanced understand ing of protein β-sheets is important be cause this protein structure is found in almost all proteins and plays a key role in protein-related illnesses such as Alzhei mer's disease and mad cow disease. To create chemical models for these β-sheet structures, Nowick and his co workers designed, synthesized, and stud ied a variety of molecular templates that can orient attached peptide strands. One
Nowick
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of these templates consists of an oli- have reached more than 25,000 students RNA structure. He established what col leagues view as a uniquely interdisciplin gourea molecular "scaffold" that can ori at about 100 high schools. Nowick has received awards for train ary program integrating organic synthe ent polypeptide chains in either parallel ing undergraduates in his research labora sis, physical organic chemistry, NMR or antiparallel β-sheet orientations. Another template he developed is a tory and for his chemistry outreach pro spectroscopy, molecular biology, and en β-strand mimic, which imitates the array grams. Other awards include a Camille & zymology to support his research in the of hydrogen-bond donor and acceptor Henry Dreyfus New Faculty Award, an interface between organic chemistry and functionality displayed on one edge of a American Cancer Society Junior Faculty biology. polypeptide in a β^-strand conformation. Research Award, a National Science Foun His work has focused on activation These components and his group's devel dation Young Investigator Award, an Ar and bond-forming reactions that trans opment of a mild way to prepare amino nold & Mabel Beckman Foundation Young form isopentenyl diphosphate into more acid and peptide isocyanates allowed a Investigator Award, a Presidential Faculty than 23,000 known metabolites. To ac means to prepare a variety of diverse Fellow Award, a Camille Dreyfus Teacher- complish this, he synthesizes substrates β-sheet structures. He has used these Scholar Award, and an Alfred P. Sloan Re and inhibitors, isolates and characterizes structures to measure the propensities of search Fellowship. genes that encode the enzymes, con various amino acids to form β-sheets. structs recombinant organisms for highIn a second area of research, Nowick C. DALE POULTER, Distinguished Pro level protein synthesis, analyzes the ki demonstrated that aqueous micelles pro fessor of Chemistry at the University of netic behavior and products of the enzy vide a microenvironment that allows mo Utah, Salt Lake City, is recognized for his matic reactions, and correlates enzyme lecular recognition through hydrogen multidisciplinary work in bioorganic structure and function. He has identified bonding in water. He is now trying to use chemistry. As a colleague puts it, "He genes that code for a variety of enzymes, this type of molecular recognition to trans stands out because he makes outstanding including enzymes that are targets for de port polar and charged molecules across contributions to many areas of chemis velopment of drugs for atherosclerosis lipid bilayer membranes—an approach try: organic synthesis, enzyme inhibitor and cancer. that promises to facilitate delivery of drugs design, [nuclear magnetic resonance] Poulter has been active on a variety of that have poor bioavailability. techniques, 'classical' enzymology, and committees, including those of the Amer ican Chemical Society, National Academy Nowick received a Ph.D. degree in molecular biology." chemistry from Massachusetts Institute of After receiving a bachelor's degree in of Sciences, and National Institutes of Technology in 1990. Following a National chemistry at Louisiana State University in Health. He has served on the editorial ad Science Foundation postdoctoral fellow 1964, Poulter went to the University of visory boards of various journals, includ ship with Julius Rebek at MIT, he joined California, Berkeley, where he earned a ing the Journal of the American Chemi the chemistry faculty at UC Irvine in July Ph.D. degree in 1967. From 1967 to 1969, cal Society, Chemical Reviews, and the 1991 as an assistant professor. He was he was a postdoctoral fellow at the Univer Journal of Organic Chemistry, where he named associate professor in July 1996. sity of California, Los Angeles. He joined has also been a senior editor. He is cur Nowick has a keen interest in chemistry the University of Utah in 1969 as assistant rently chair-elect of the ACS Organic education for young people. He founded professor in the department of chemistry. Chemistry Division. the MIT Chemistry Outreach Program and At various times, he has concurrently been Poulter has also been on the organiz developed the UC Irvine Chemistry Out on the faculties of the departments of bio- ing committees of the 13th and 14th En reach Program, both aimed at bringing the pharmaceutical sciences, biochemistry, zyme Mechanisms Conferences, chairing excitement of chemistry to high school and medicinal chemistry; he was named the committee for the 14th, during students. He obtained funding for the pro chairman of the department of chemistry 1993-95. He has won a variety of other grams—which send graduate students in 1995 and Distinguished Professor of awards, including ACS's Ernest Guenther into high school classrooms—from the Ca Chemistry in 1996. Award in the Chemistry of Natural Prod mille & Henry Dreyfus Foundation and Poulter's pioneering work has been in ucts; the Utah Award of the ACS Salt from the National Science Foundation. the areas of the biosynthesis of natural Lake Section; and the Utah Governor's Thus far, the UC Irvine and ΜΓΓ programs products and determination of transfer- Medal in Science & Technology. FEBRUARY 23, 1998 C&EN 87
awards The extraordinary depth and breadth of SCOTT D. RYCHNOVSKY'S research have established the University of California, Irvine, chemistry professor as a leading organic chemist less than 10 years into his independent academic career. His accomplishments in the area of polyene macrolide antibiotics are particularly notable. "There was never the slightest doubt that Rychnovsky was going to be a major contributor to the field of organic synthesis," one colleague writes. "The scope, originality, and significance of his achievements have exceeded even these high expectations." Rychnovsky's achievements in research on polyene macrolides (the complex antifungal compounds produced by Streptomyces soil microorganisms) range from structure determination to total synthesis. He developed a nuclear magnetic resonance method for determining the detailed stereochemistry of the molecules by exploiting the fact that they can be thought of as a series of 1,3-glycols. The technique is based on two-dimensional NMR analyses of 13C-labeled acetonide derivatives of the polyols. In the area of synthesis, Rychnovsky has devised a powerful new strategy for joining the carbon atoms that form the backbone of the macrolides. In his convergent approach, 4-cyano-l,3-dioxanes are used to link fragments through nitrile alkylation, which is followed by reductive decyanation. Rychnovsky received a B.S. degree in chemistry from the University of California, Berkeley, in 1981 and a Ph.D. degree in chemistry in 1986 from Columbia University, where his research adviser was Gilbert Stork. After National Institutes of Health postdoctoral fellowships at Harvard University and Yale University, he joined the faculty of the University of Minnesota, Minneapolis, as an assistant professor in 1988. He moved to UC Irvine as a full professor in 1995. Among his other honors, Rychnovsky has received a Camille Dreyfus TeacherScholar Award (1990-95) and a National Science Foundation Presidential Young Investigator Award (1991-96). He was named an Alfred P. Sloan Research Fellow (1992-94). He currently holds an NIH Research Career Development Award. Imaginative, insightful, creative. Those are just a few of the laudatory words that have been used to describe JAY S. SIEGEL. Having embarked on independent research only 12 years ago, this 38-year-old 88 FEBRUARY 23, 1998 C&EN
chemistry professor at the University of California, San Diego, already is a recognized authority in stereochemistry and molecular design. The unique properties of aromatic molecules seem to have a special fascination for Siegel. Some of his recent contributions in the Walsh chemistry of aromatic systems are challenging established ideas, prompting a colleague to predict that "his recent work will cause changes to be made in textbooks." Believing that localized electrons in aromatic systems such as benzene could lead to new reactivities, Siegel joined the ranks of scientists who have been trying to find ways to localize the pi electrons of—and thus impose bond alternation in— benzene. On the basis of theoretical calculations, he predicted in 1992 that bond-localized arènes, or cyclohexatrienes, can be made by attaching strained bicyclic rings to benzene. The idea was met with skepticism, but within three years, he prepared and characterized compounds that proved him right. And by 1996, the principle was applied to larger aromatic systems (C&EN, April 1, 1996, page 27). The work established a new paradigm for perturbing the structure—and hence modifying the reactivity—of aromatic systems. And in quintessential Siegel fashion, the research combined powerful computational methods with synthetic methodology and rigorous structural characterizations. His group has adeptly used this approach to assemble molecules of high molecular weight and complexity. Recent examples include syntheses of "Kuratowski cyclophane," a topologically complex molecule with intricate molecular connectivities, and of the fullerene fragment corannulene. Another contribution is elucidation of noncovalent interactions of aromatic systems. Contrary to the general view that aromatic systems are nonpolar and hydrophobic, Siegel has shown that aromatic systems exert an electrostatic, socalled polar/π, effect through space. Thus, the chemistry of aromatic rings should reflect both polar and nonpolar
Wipf
effects. Aromatic noncovalent interac tions being ubiquitous in areas as diverse as protein folding and drug design, this work likely will have wide influence, says a colleague. As a communicator of science, Siegel is also much admired. He "explains his science in clear terms and with great re gard and respect for his audience," says a colleague. Although the primary mission of scientists is "to produce excellent re search," this colleague says, "it is also es sential to communicate our results to our colleagues. In both facets, Jay excels." Siegel received a B.S. degree in chem istry from California State University, Northridge, in 1980. He obtained M.A. and Ph.D. degrees in chemistry from Princeton University in 1982 and 1985. He joined the faculty of UCSD in 1986, rising through the ranks to full professor in 1996. CHRISTOPHER T. WALSH has built a career by taking the principles of physi cal organic chemistry, with its emphasis on understanding the mechanisms of re actions, and applying them to solve med ical problems. The Walsh approach has been to study important biological systems by focusing on the mechanism of action of a key en zyme, using that information to design en zyme inhibitors, and then studying the de velopment of bacterial resistance to these inhibitors. Walsh and his students have used this approach, for example, to probe the way bacteria synthesize their cell walls, a process that can be interrupted by the antibiotic vancomycin. In recent years, the Walsh group has carried its under standing of this system a step further by identifying all of the genes involved, in cluding those for the proteins that control gene expression as well as for the en zymes themselves.
Walsh's group has applied the same approach to elucidate the mechanisms of enzymes that useflavins,nickel, and vita min Κ as cofactors; proteins that are tar gets of immunosuppressive agents; the enzyme that certain bacteria use to de toxify mercury; and, most recently, sys tems responsible for nonribosomal pep tide synthesis. Walsh, who since 1991 has been Ham ilton Kuhn Professor in the department of biological chemistry and molecular pharmacology at Harvard University Medical School, has spent his career at the intersection of organic chemistry, bi ology, and medicine. "He has arguably been the foremost individual in convinc ing the organic chemical community to look to biology and medicine for new frontiers," a colleague says. "Just as im portant, Chris has convinced the biologi cal and medical research communities that organic chemistry is an important partner in their enterprise." Walsh joined Harvard in 1987 to be the first chairman of a new medical school department formed by combining the departments of biological chemistry and pharmacology. It was a position he held until 1995. From 1992 to 1995, he was also president of the Dana-Farber Cancer Institute, a cancer research hospi tal affiliated with Harvard Medical School. He received a bachelor's degree from Harvard in 1965 in biology and a Ph.D. degree in life sciences from Rockefeller University, New York City, in 1970. Fol lowing two years of postdoctoral study in biochemistry at Brandeis University, he joined the chemistry faculty of Massa chusetts Institute of Technology in 1972, becoming a professor of chemistry and biology in 1978. He was chairman of MIT's chemistry department from 1982 to 1987. A member of the National Academy of Sciences, the Institute of Medicine, and the American Academy of Arts & Scienc es, Walsh was also the recipient of the ACS Division of Biological Chemistry's Eli Lilly Award in Biochemistry in 1979. During the first seven years of his career, PETER WIPF of the University of Pitts burgh "completed 10 total syntheses of complex natural products, many of which are of fundamentally new struc tural types," a colleague writes. "He has reported numerous examples of innova tive protocols for the preparation of heterocycles that are now the methods of choice applied by many researchers in
industry and academe. His discoveries of novel organometallic protocols have earned him a reputation as a world lead er in organozirconium chemistry." One example of Wipf s combined techniques is his synthesis of (+>curacin A, a marine natural product that shows activity against cancer. The compound is an acid-, base-, and oxidation-sensitive 2-cyclopropylthiazoline with a 15-carbon etraene side chain at position 4 and must be stored below -80 °C under inert gas. To cobble together the side chain, Wipf added bis(cyclopentadiene)chlorozirconium hydride across an acetylene and, in one of his organometallic innova tions, switched the zirconocene group with the more active zinc by reaction with diethylzinc. In situ addition of the organozinc species to an aldehyde, fol lowed by further chain extension via a second organozirconocene intermediate, completed the preparation of the sidechain skeleton. After segment condensation, Wipf used his oxazoline-thiazoline conversion strategy and his polymer-linked cyclodehydrating reagent to obtain the sensitive heterocycle moiety in the final step of the synthesis. In his synthesis of hennoxazole A, a compound from the sea sponge that is active against herpes simplex virus, Wipf knew from the prior work of others the relative configurations at three of the five stereocenters, but not the configuration at any one carbon atom. The compound has two oxazole rings bonded to one an other in the middle of the molecule, so he devised new ways to make such rings. After the completion of the conver gent synthesis of one of the eight possi ble stereoisomers, he turned to instru mental techniques to elucidate the config uration of the natural product. Circular dichroism analysis of the natural product, the synthetic compound, and synthetic fragments allowed the assignment at the remote C-22. Next, he used van't Hoffs principle of the additive properties of molar rotation angles to confirm his pro posed configurations at all stereogenic carbons. Wipf received a four-year diploma in chemistry at the University of Zurich in 1984 and a Ph.D. degree with organic chemistry professor Heinz Heimgartner there in 1987. After two postdoctoral years with organic chemistry professor Robert E. Ireland at the University of Vir ginia, Charlottesville, Wipf joined the fac ulty at Pittsburgh in 1990.^
Goto
Pittcon '98 without leaving the comforts of your mouse. Here's how you can make the most of your time before, during, and after this year's Pittsburgh Conference. Just click on Pittcon '98 on the Web and you'll be able to: • Browse the advance Conference program. • Find out which companies are exhibiting and where to find their booths. • Learn about new product announcements. • Discover which technical papers are being presented. • Get a description of the short courses and other activities offered at the Conference. If you're planning to attend Pittcon '98, this service gives you a head start so you can use your time there wisely. If you're going to miss the Conference, you won't really miss it after all, because the Pittcon '98 Website offers so much valuable information. Access to Pittcon '98 on the Web is free-but for a limited time only. Bookmark it today:
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awards
ACS Women Chemists Committee Travel Awards The American Chemical Society Women Chemists Committee has awarded several travel grants to cover expenses associated with attending scientific meetings to be held between Jan. 1 and June 30. Undergraduate, graduate, and postdoctoral women chemists who wish to present the results of their research at a scientific meeting are eligible for these grants. The grants are funded by Eli Lilly, Hoechst Celanese, and the ACS Division of Industrial & Engineering Chemistry. The 14 recipients are as follows: Emily C. Chopko, undergraduate student in chemistry at St. Joseph's University, Philadelphia. She received $600 to attend the ACS national meeting in Dallas, where she will present "Molecular Structure of 1-Substituted Bicyclo[2.2.0]hexanes." Jennifer I. Epperlein, undergradu-
ate student in chemistry at the University of Vermont, Burlington. She received $660 to attend the ACS national meeting in Dallas, where she will present "Cobalt and Copper Incorporation into Mesoporous MCM-48." Michelle O. Fletcher, Ph.D.-degree student in organic chemistry at the University of Florida, Gainesville. She received $660 to attend the ACS national meeting in Dallas, where she will present "Kinetic Study on the Dealkylation Reaction of Iodide on Ammonium Salts." Allison L. Hurley, Ph.D.-degree student in organic chemistry at Wake Forest University, Winston-Salem, N.C. She received $610 to attend the ACS national meeting in Dallas, where she will present "Reactions of Transition-Metal Propargyl and Allenyl Complexes with Sulfur Dioxide and Transition-Metal Bond-Cleaving Reactions of Cycloadducts That Yield Cyclic Sulfenate Esters." Kimberly B. Johnson, master's degree student in chemistry at Virginia Commonwealth University, Richmond. She received $300 to attend Pittcon '98 in New Orleans, where she will present
"Chemometric Study of the Degradation of Sulfonylurea Herbicides Using LC/ DAD/MS." Jennifer E. Lewis, Ph.D.-degree student in chemistry at Pennsylvania State University. She received $500 to attend the ACS national meeting in Dallas, where she will present "Experimental Study of the Solute Dependence of Local Density Augmentation." Allison L. Marlow, Ph.D.-degree student in organic chemistry at the University of Maryland, College Park. She received $580 to attend the ACS national meeting in Dallas, where she will present "Phase-Transfer Catalysis with SelfAssembled Ionophores." Elizabeth C. Moll, undergraduate student in chemistry at Middle Tennessee State University, Murfreesboro. She received $450 to attend the ACS national meeting in Dallas, where she will present "4-Phenylbicyclo(2.2.2)octyl Groups in Self-Assembled Films." Stacy A. O'Neill, Ph.D.-degree student in organic chemistry at North Carolina State University, Raleigh. She received $600 to attend the ACS national
ARTICLES A S A P . It's like being in a time machine on fast forward.
Welcome to the world of real-time science. Beginning in January 1998, ACS Web Edition subscribers will enjoy an exciting new service, Articles ASAPSM. The American Chemical Society will post articles from its 26 prestigious research 90 FEBRUARY 23, 1998 C&EN
journals on the Web "As Soon As Publishable." This means access to complete, peer-reviewed, fully edited, scientific articles — not abstracts, not pre-prints — 2 to I I weeks earlier than they are available J^J^ \ in print.
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meeting in Dallas, where she will present "Ririg-Closing Metathesis of a-Alkoxystannanes: A Facile Route to Substituted Cyclic Esters." Anna V. Rotberg, undergraduate student in chemistry and neuroscience at Amherst College, Amherst, Mass. She received $550 to attend the Biophysical Society Conference in Kansas City, Mo., where she will present "Calmodulin Trapping and Autophosphorylation in Calcium/Calmodulin-Dependent Protein Kinase II." Jennifer L. Sebestl, Ph.D.-degree student in inorganic chemistry at Wayne State University, Detroit. She received $690 to attend the ACS national meeting in Dallas, where she will present "Synthesis, Structure, and Reactivity of Three-Coordinate Magnesium Amide Complexes." Roberta A. Sulk, Ph.D.-degree student in analytical chemistry at the University of Wyoming, Laramie. She received $800 to attend Pittcon '98 in New Orleans, where she will present "SERS Coatings for the Detection of Illicit Drugs." Mary B. Walsh, undergraduate student in chemistry at Villanova University,
Villanova, Pa. She received $660 to attend the ACS national meeting in Dallas, where she will present "Studies of Heterocyclic Ring-Openings Using DensityFunctional Theory." Molly Warmoth, undergraduate student in chemistry at Furman University, Greenville, S.C. She received $640 to attend the ACS national meeting in Dallas, where she will present "Charge-Transfer Complexes of Pyridine."^
Dixon wins Harry & Carol Mosher Award Joseph A. Dixon, emeritus professor of chemistry at Pennsylvania State University, is the recipient of the 1997 Harry & Carol Mosher Award given by the ACS Santa Clara Valley Section. The award— which consists of $2,000 and a plaqueis given annually to recognize and encourage work in chemistry, to advance chemistry as a profession, and to recognize service to ACS. Dixon was on the faculty at Pennsyl-
Dixon vania State University from 1947 to 1950, and then became a research chemist at Standard Oil Co. of California, a position he held until 1952. In 1953, he moved to Lafayette College, Easton, Pa. He returned to Penn State in 1955 and re-
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