AWARDS
ACS 1990 Award Winners Following are vignettes of the Arthur C. Cope Award winner and 10 recipients of Arthur C. Cope Scholar Awards. They will receive their awards at the annual Arthur C. Cope Symposium organized by the ACS Division of Organic Chemistry. The symposium will be held in Washington, D.C., during the ACS national meeting Aug. 26-31,1990. The Arthur C. Cope Scholar Awards recognize and encourage excellence in organic chemistry. Each award consists of a certificate and a $20,000 unrestricted research grant to any university or nonprofit institution designated by the recipient. The recipients are required to deliver a lecture at the Arthur C. Cope Symposium.
Arthur C. Cope Award KOJI NAKANISHI is noted by a colleague as a "scientist of extraordinary breadth." He is currently Centennial Professor in the departm e n t of chemistry at Columbia University. One of Nakanishi's recent areas of research has been with the process of vision, specifically, retinal proteins, and has led to a widely accepted hypothesis that has helped in understanding the importance of electrostatic interactions within binding sites. His further research has shown that incubation of blind mutants of the green algae Chlamydomonas with retinal analogs results in predictable shifts in their phototactic maxima.
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Significantly, this information demonstrated not only that behavioral shifts can be induced by retinal analogs, but also that these algae could be used for rhodopsin studies. Another realm of Nakanishi's research has resulted in devising a new circular dichroic micromethod for determining glycosidic linkages in oligosaccharides that requires no reference compounds. Nakanishi's third active field of research is spectroscopy, where he has been a leader in the study of organic molecules. Although the isolation and structural studies of bioactive molecules have interested him throughout his career, Nakanishi's focus recently has been on clarification of the interaction between bioactive molecules and receptor biopolymers. A prolific writer as much as a proficient scientist, Nakanishi is credited with more than 480 published papers and has coauthored or edited four books. Nakanishi received both B.S. (1947) and Ph.D. (1954) degrees from Japan's Nagoya University, and then went to Harvard University for postgraduate work from 1950 to 1952. His career has included professorships at universities in Japan as well as at Columbia, where he has been since 1969. Concurrently, Nakanishi is director of Suntory Institute for Bioorganic Research in Osaka, Japan. From 1967 to 1977 he directed research in Kenya at the International Centre of Insect Physiology and Ecology. The Cope award certainly is not the first time Nakanishi has been recognized for his work. Other honors include the Ernest Guenther Award from ACS in 1978; Chemical Society of Japan Award in 1979; the Remsen Award from the ACS Maryland Section in 1981; Research Achievement Award, American Society of Pharmacognosy, 1985; the Paul Karrer Gold Medal, University of Zurich, 1986; and the Egbert Havinga Medal, Leiden University, the Netherlands, 1989.
Arthur C. Cope Scholar Awards EDWARD M. ARNETT's vital role in the development of physical organic chemistry and his leading contributions are being recognized by this award. During the past 30 years, Arnett, R. J. Reynolds Professor of Chemistry at Duke University, has attempted to deal with the fundamental questions of structure and reactivity as they are manifested in all kinds of acid-base reactions and their modulation by intermolecular forces, such as those that determine solvent effects in organic chemistry. In his research, he has emphasized thermodynamic analyses of organic reactions as a necessary complement to kinetic-mechanistic investigations. Arnett's work on solvation effects in organic chemistry changed previous views of the principal causes of important reactivity sequences and clarified the fundamentals of solvation effects. Arnett has put calorimetry to use for physical organic chemistry and invented a number of new and elegant techniques for using it to get at important questions. More recently he and his research group have used solution calorimetry to extend the understanding of acid-base behavior in solution to solid acids and bases. In his research on chiral surfactants in monolayers he combined stereochemistry with Langmuir monolayer technique for observing and manipulating the orientation of molecules in two dimensions at a plane surface, and his group has established the conditions for molecular recognition at a surface in enantiomeric and diastereomeric combinations of chiral surfactants. In yet another pioneering research effort, Arnett and his group initiated a full-scale study of thermodynamic, structural, and kinetic processes of enolate and aldol reactions. Born in Philadelphia, Arnett attended the University of Pennsyl-
Arnett vania. He received a Ph.D. degree there in 1949. Upon graduation he joined Max Levy & Co., where he served as research director until 1953. From there he went on to teach at Western Maryland College for two years, followed by a twoyear stint as a research fellow with Paul D. Bartlett's group at Harvard University. In 1957, he returned to teaching, joining the faculty of the University of Pittsburgh; he remained there until 1980, at which point he moved to Duke University. Among his awards are the James Flack Norris Award in Physical Organic Chemistry (1977), the ACS Award in Petroleum Chemistry (1985), and the 4th Annual Allen Day Award of»the Philadelphia Organic ChemisteCUib (1986). He was elected to the National Academy of Sciences in 1983.
"There are few other academic scientists, if any, who combine PAUL A. BARTLETT's ability to design, synthesize, and evaluate biologically interesting molecules." So says an admiring colleague in summing up this award winner's achievements in organic synthesis and bioorganic chemistry. Bartlett is professor of chemistry at the University of California, Berkeley. Perhaps the best word to characterize Bartlett's work in organic synthesis is variety. Nearly every one of his publications has addressed an independent topic. And there is nothing routine or derivative in character in his research. For instance, the award winner took the rather workaday concept of electrophilic cyclization of unsaturated oxygen compounds and turned it into
Bartlett
Grieco
Grubbs
Bartlett has served as a consulimportant approaches for the stereocontrolled synthesis of lactones, acy- tant and on the scientific advisory clic epoxy alcohols, and cyclic ethers. boards of a number of corporations, New synthetic methods as well as as well as on the Bioorganic and conceptual approaches are mani- Natural Products Study Section of fested in Bartlett's total syntheses, the National Institutes of Health. from his first—brefeldin A—to his He is currently a member of the more recent—tirandamycin. These editorial advisory boards of The Joursyntheses include a-multristriatin, nal of Organic Chemistry and Bulletin poly ether subunits, and nonactin. de la Societe Chimique de France. He His total synthesis of nonactin is has lectured widely and has more particularly impressive, in that the than 100 publications to his credit. antipodal subunits were synthesized from a single optically active precursor purely by manipulating a cy- PAUL A. GRIECO has a long list of clization step late in the sequence. major accomplishments in the broad Bartlett's most recent contribu- range of natural products chemistions are in bioorganic chemistry. try, and his research has had a noteHis research in this area is focused worthy impact on the field. "He is on the development of phosphorus a highly creative and highly procompounds as transition-state ana- ' ductive scholar who clearly deserves log inhibitors of hydrolytic enzymes, the recognition and distinction that and on elucidating the mechanisms this award brings," says a close asand inhibitors of enzymes in the sociate. Grieco is Earl Blough Proshikimic acid biosynthetic pathway. fessor of Chemistry at Indiana UniIn his work on phosphorus ana- versity, Bloomington, as well as logs, for example, he has provided chairman of the d e p a r t m e n t of a standard for the intrinsic binding chemistry. energy to be attributed to a hydroGrieco obtained a B.A. degree gen bonding moiety in an enzyme- (1966) from Boston University, and inhibitor complex. His studies of M.A. (1967) and Ph.D. (1970) deintermediates in the shikimic acid grees in organic chemistry from Copathway served as the basis for the lumbia University. In 1970-71 he synthesis of novel inhibitors and was a National Science Foundation putative intermediates for a num- postdoctoral fellow at Harvard Uniber of enzymes. versity. In 1971 he joined the faculThe award winner received B.A. ty at the University of Pittsburgh as and M.A. degrees in chemistry from assistant professor and rose to proHarvard University in 1969, and a fessor in 1977. He moved to IndiPh.D. in organic chemistry from ana University as professor in 1980 Stanford University in 1972. He then and assumed his present post in spent a year as a postdoctoral fel- 1985. low at the University of California, One of Grieco's major focuses has San Diego. Bartlett joined the facul- been the synthesis of terpenoids. ty at UC Berkeley as assistant pro- His early studies in this group of fessor in 1973. He assumed his natural products led to the total synpresent position in 1982. thesis of vernolepin, vernomenin, October 23, 1989 C&EN
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Awards
Heathcock
Jorgensen
eriolanin, eriolangin, ambrosin, damsin, helenalin, psilostachyin C, mexicanin I, linifolin A, bigelovin, and various prostaglandin derivatives. Key to many of these syntheses is the use of a bicyclo[2,2,l]heptane nucleus as a stereochemical control vehicle. In recognition of this work, he received in 1981 ACS's Ernest G u e n t h e r Award in the Chemistry of Essential Oils & Related Products. This strategic approach of using a bicycloheptane nucleus as a stereochemical control template was extended in Grieco's classic synthesis of compactin and also in the preparation of several members of the macrolide/polyether antibiotic group (methynolide, calcimycin, and tylonide, among others) where stereochemical data built into the bicycloheptane nucleus were transformed into the stereochemistry of acyclic molecules. More recently he has led the way in the synthesis of complex quassinoids, accomplishing the first total syntheses of quassin, castelanoide, and klaineanone. In another research program, the award winner initiated a series of synthetic studies of organic reactions in aqueous media. Focusing on aqueous Diels-Alder reactions, he has developed methods for synthesizing early intermediates in the quassinoid program. These methods also have been applied to a novel synthesis of the Inhoffen-Lythgoe diol. These accomplishments, says a colleague, "underscore Grieco's versatility and ability to move into new areas and make immediate, significant contributions." Grieco has been a guest lecturer at a number of universities and has 44
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Schultz
received numerous honors. In addition to the Ernest Guenther Award, he received the National Cancer Institute's NIH Merit Award in 1988 and the ACS Akron Section Award in 1982. ROBERT H. GRUBBS' research has been marked by an unusual degree of innovation, particularly in applying organometallic chemistry to new areas. "He was one of the first people to recognize the potential impact of physical organic techniques in organometallic chemistry," points out a colleague. Grubbs is professor of chemistry at California Institute of Technology. A native of Kentucky, Grubbs obtained B.S. (1963) and M.S. (1965) degrees at the University of Florida, and a Ph.D. (1968) degree in organic chemistry at Columbia University under Ronald Breslow. In 1968-69, he did postdoctoral work at Stanford University with James Collman. He joined the faculty at Michigan State University in 1969 as assistant professor, and moved to Caltech in 1978 as professor. One of Grubbs' most significant early contributions, during his years at Michigan State, was the synthesis of t h e first optically active cyclobutadiene complexes and the use of these complexes to detect free cyclobutadiene in the oxidative decomposition of cyclobutadieneiron tricarbonyl complexes. He followed this important work with the synthesis and study of some of the first known saturated metallacyclic complexes, primarily in the bis(phosphine)nickel series. His increasing interest in the olefin metathesis reaction led to studies of the interface
between organometallic and polymer chemistry. This reaction interchanges the carbons of two reacting alkenes and, when applied to cyclic systems, functions as a highly efficient alkene polymerization method. One of the shortcomings of the olefin metathesis reaction, however, was the difficulty of isolating and purifying the true catalyst. Following his move to Caltech in the late 1970s, Grubbs went to work to solve this problem by preparing isolable and characterizable compounds that would undergo the reaction. He found that the aluminum moiety of a titanium-methylene-aluminum complex could be removed from the metal center to generate a reactive titanium methylene complex. His investigation snowed that this complex reacts reversibly with alkenes to give titanacyclobutanes, providing a well-characterized model for the critical step in olefin metathesis. Grubbs' continuing interest in organometallic and polymer chemistry has resulted in another noteworthy discovery: living polymers with metallic end groups. His research into these macromolecular materials is providing fundamental knowledge about the mechanism of metal-mediated polymerizations. The award winner's most recent disc o v e r y is cationic ruthenium complexes that rapidly catalyze ringopening metathesis polymerizations in water solution. In addition to numerous visiting lectureships, Grubbs has been a consultant for several major chemical companies, including Dow, Monsanto, and Du Pont. He received the 1988 ACS Award in Organometallic Chemistry. He was elected to the National Academy of Sciences in 1989. CLAYTON H. HEATHCOCK has been a leading researcher in the field of organic synthesis for the past 20 years. His pioneering studies of the stereochemistry of enolate reactions and his novel methods for efficient synthesis of complex polycyclic natural products have earned him this award. Heathcock is professor of chemistry at the University of California, Berkeley.
Among the award winner's most significant contributions has been his work on acyclic stereoselection. In 1977, Heathcock and his coworkers Charles Buse and William Kleschick showed that in many cases there is a strong correlation between the stereochemistry of an enolate and that of the 0-hydroxy ketone or ester that results from the enolate's reaction with an aldehyde. The following year, Heathcock and Buse reported similar diastereoselectivity in the reactions of crotylchromiWender Stille Wasserman um(II) compounds with aldehydes, a discovery that laid the groundHeathcock has earned numerous in solution, computer simulations work for much subsequent work on h o n o r s , i n c l u d i n g ACS's Ernest had been carried out only for some control of stereochemistry with oth- Guenther Award in the Chemistry simple liquids. Jorgensen's group er crotylmetal reagents. He and his of Essential Oils & Related Products now has modeled many complex coworkers also demonstrated that in 1986 and the 1990 ACS Award organic liquids and solutions and stereoselectivity can be obtained in for Creative Work in Synthetic Or- has helped develop the technology the reactions of certain a-alkoxyester ganic Chemistry. He has served on to facilitate such studies. The reenolates, thus providing a way to the editorial board of Organic Syn- search depends critically on the introduce lactic acid synthons in theses and was editor-in-chief in availability of accurate intermolecmacrolide and polyether syntheses. 1986. Currently Heathcock is editor- ular potential functions. Jorgensen Another key finding by Heath- in-chief of The Journal of Organic has developed functions for water, organic molecules, ions, and procock and his associates was that Lew- Chemistry. teins. Related investigations have is acid mediated additions of enol been seminal in establishing viable silanes to chiral aldehydes proceed methodology for computations of with unusually high diastereofacial WILLIAM JORGENSEN, Herbert free energy changes in solution. selectivity. He proposed a theory C. Brown Professor of Chemistry, based on trajectory analysis to ex- Purdue University, "is the chief pi- Novel applications have included plain the unexpected selectivity. The oneer of theoretical studies of or- studies of ion pairing, conformatheory was later verified computa- ganic chemistry in solution," accord- tional equilibria, pK a s of weak organic acids, partition coefficients, tionally and by further experiments. ing to a colleague. He is a major and binding affinities. Jorgensen is Heathcock's group also has devel- contributor to the development of oped applications of this synthesis computer modeling of complex, also known for many molecular orbital investigations of organic remethod, including the syntheses of condensed-phase systems, and he activity. ristosamine, cladinose, the vitamin has advanced the understanding and E side chain, and the C-40 archae- m o d e l i n g of solvent effects on Previous honors include the 1986 bacterial diol. conformational equilibria, reaction Annual Medal of the International More recently Heathcock's group surfaces, and host-guest complexa- Academy of Quantum Molecular Scihas focused its efforts on another tion. He is also a major figure in ences, a Camille and Henry Dreyfus basic organic process, the Michael computer synthesis. The Cameo pro- Foundation Teacher-Scholar award addition reaction. The team has gram from his research group is a for 1978-83, and an Alfred P. Sloan largely delineated the stereochemi- valuable tool for the interactive pre- Foundation fellowship for 1979-81. cal outcome of the Lewis acid medi- diction of molecular properties and He serves on several advisory ated process and the lithium enolate products of organic reactions. boards, including those of the Jourversion. Further, it has established The award winner graduated from nal of the American Chemistry Society a previously unknown relationship Princeton University with a B.A. in and the Journal of Physical Organic between enolate geometry and Mi- chemistry in 1970. He completed a Chemistry. chael addition stereochemistry. Ph.D. in chemical physics in 1975 Heathcock received a Ph.D. degree under E. J. Corey at Harvard Unifrom the University of Colorado, versity, and then joined the faculty PETER G. SCHULTZ, professor of Boulder, in 1963. He spent the fol- of the department of chemistry at chemistry, University of California, lowing year as a postdoctoral fel- Purdue, where he was made full Berkeley, has "literally burst upon low at Columbia University. In 1964 professor in 1982. From 1984 to 1987 the national chemistry scene," says the award winner moved to UC he was head of Purdue's organic a colleague. Schultz's doctoral theBerkeley as assistant professor. He chemistry division. His present ti- sis, under preceptor Peter B. Dervan at California Institute of Technolobecame professor in 1975, and tle was conferred in 1985. served as chairman of the departWhen Jorgensen began his theo- gy, showed for the first time that ment from 1986 to 1989. retical work on organic chemistry synthetic molecules could cleave October 23, 1989 C&EN
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Awards DNA site-specifically and earned him the Nobel Laureate Signature Award for Graduate Education in Chemistry (1984). Schultz joined Berkeley in 1985. The award winner was among the first to discover that antibodies could be used as catalysts. In their latest work, he and his team are introducing catalytic groups directly into antibody c o m b i n i n g sites by sitedirected mutagenesis, chemical modification, and antibody-hapten complementarity. Using cleavable affinity labels, they have successfully placed synthetic catalytic groups (nucleophiles) and reporter molecules (fluorophores) into antibody combining sites. This work may lead to the ability to tailor-make catalysts for applications in biology, chemistry, and medicine. Going beyond the scope of sitedirected mutagenesis, Schultz has rationally modified enzyme specificity by fusing entire catalytic and binding domains to produce hybrid enzymes. By selectively introducing an oligonucleotide binding site into a relatively nonspecific phosphodiesterase he and his team have prepared new enzymes capable of sequence-specifically cleaving RNA and single-stranded and duplex DNA. This approach not only offers a powerful tool for studying DNA and RNA but is a springboard for the design of other selective hybrid enzymes. In other research, Schultz's group has developed methodology for replacing specific amino acid residues in proteins with synthetic amino acid analogs. They are investigating the effects of incorporating into proteins non-naturally occurring amino acids with novel steric, electronic, and spectroscopic properties. This young scientist's accomplishments have earned him, among other honors, Alfred P. Sloan fellow (1988), Alan T. Waterman Award (1988), and ACS Award in Pure Chemistry (1990). JOHN K. STILLE, who was killed July 19 in a plane crash, was one of the world's foremost synthetic polymer chemists. Stille was selected as a Cope Scholar and he accepted the award before his untimely death. 46
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The $20,000 research grant accompanying this award will be granted to Colorado State University, where Stille was Distinguished Professor, to carry on his work. The research achievements of Stille encompass two major areas of chemistry: polymer and organic— particularly organometallic chemistry and catalysis and their application to organic synthesis. Two of his most important contributions are the palladium-catalyzed coupling reactions of organotin reagents with organic electrophiles and a newly discovered hydroformylation catalyst. The coupling reaction already has had a significant impact on synthetic organic chemistry, since it is among the most versatile methods of carbon-carbon bond formation. It is being used widely for the synthesis of complex organic molecules, particularly in the pharmaceutical industry. An active member of ACS, Stille was chairman of the Iowa Section in 1965, chairman of the ACS Biennial Polymer Symposium in 1972 and 1974, and chairman of the Division of Polymer Chemistry in 1975. From 1974 to 1977, he was a member of the evaluation panel for the polymer division, Institute for Materials Research, of what was then the National Bureau of Standards. In 1979-80, he was project coordinator for Homogeneous Catalysis by Organometallic Compounds, part of the Joint U.S./U.S.S.R. Agreement in Science & Technology's catalysis program. More recently, he was a committee member of the International Union of Pure & Applied Chemistry's macromolecular division. He was associate editor of Macromolecules from 1967 to 1981, associate editor of the Journal of the American Chemical Society from 1982 to 1987, and was on the editorial advisory board of Organometallies at the time of his death. He also enjoyed teaching, and at various times was a visiting professor at the Royal Institute in Stockholm and a U.S.S.R. Academy of Sciences tour speaker. Stille had a lifelong commitment to polymer and materials research. He was a consultant for Du Pont for many years, and an adviser to the National Aeronautics & Space
Administration for five years. He won the 1982 ACS Award in Polymer Chemistry and the 1988 Colorado Section Award in Chemistry. According to one admiring colleague, HARRY H. WASSERMAN, Eugene Higgins Professor of Chemistry, Yale University, has "creatively traversed the terrain of organic chemistry from structure determination and biosynthesis, to mechanisms, synthetic methods, and total syntheses." His contributions to /5-lactams go back 30 years, beginning with his synthesis of homopenicillin. In the late 1970s, Wasserman expanded a known method for coupling /3-amino ester equivalents with cyclic imino ethers into a general procedure leading to ring expansion by selective reduction of the intermediate dihydropyrimidone. This method allowed wide flexibility in the choice of the /3-lactam component and formed the basis for the synthesis of several complex natural products in the spermine alkaloid field. More recently, his work with vicinal tricarbonyl systems and singlet oxygen has added new methodology to organic synthesis. Wasserman received his undergraduate education at Massachusetts Institute of Technology, where he was a Cambridge Scholar. After earning a B.S. degree in 1941, he matriculated at Harvard University, where he received an M.A. degree in 1942 and a Ph.D. in 1949. He joined the faculty at Yale University in 1948, was made full professor in 1962, and was named Eugene Higgins Professor in 1982. He was chairman of Yale's chemistry department from 1962 to 1965, and director of the division of physical sciences at Yale from 1972 to 1975. Winner of the 1987 ACS Award for Creative Work in Synthetic Organic Chemistry, Wasserman has also been honored for his work as a teacher. In 1985, he was the recipient of the Yale College Teacher Award and the Chemical Manufacturers Association's Catalyst Award for outstanding teaching. One colleague notes that Wasserman's unContinued on page 54
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Continued from page 46 dergraduate course in organic chemistry is one of the most popular at Yale College. He adds, " H e has earned for the course, for himself, and for the profession of chemistry, the respect, the admiration, and the affection of generations of Yale students." He has also earned the respect of organic chemists for his long-term American editorship of Tetrahedron from 1960 to 1980, and Tetrahedron Letters from 1960 to the present. He has been editor of Tetrahedron Symposia in Print since 1980. Wasserman is a member of the National Academy of Sciences. PAUL A. WENDER, professor of chemistry, Stanford University, has pioneered the development of new methodologies for the design and construction of complex organic molecules, both naturally occurring and synthetic. His contributions cover an extraordinarily broad range of chemistry, including synthetic organic, organometallic, photo-, medicinal, and agricultural chemistry; cancer biology; and computer applications in synthesis and drug design. The award winner is particularly well known for his chemical syntheses through arene-olefin photocycloadditions. In this novel and efficient approach, complex organic molecules are neatly built up via relatively high-energy activation of otherwise stable and unreactive benzene ring moieties through ultraviolet irradiation, followed by reaction of the activated species with a selected organic reactant. The methodology has proved to be extremely
versatile and has led to the elegant total synthesis of a variety of natural products difficult to synthesize by more traditional routes as well as to materials of theoretical interest. The power and efficiency of the methodology are aptly illustrated by Wender's three-step synthesis of (i)-silphinene. In other work, the award winner devised the technique of macroexpansion, by which verylarge-ring organic molecules are derived, via rearrangement of carbons, from smaller ring compounds. Using computer molecular modeling programs to study the molecular mechanism of carcinogenesis and the relationship between tumor promotion and protein kinase C (PKC), Wender achieved a number of "firsts." Among them: first synthetic route to the ABC ring systems of tigliane promoters, first rationally designed activator of PKC, and first synthesis of phorbol. Wender received a B.S. degree from Wilkes College (1969) and a Ph.D. from Yale University (1973). His honors include outstanding graduate, Wilkes College (1969), Alfred P. Sloan Foundation fellow (1979-81); Camille & Henry Dreyfus Teacher-Scholar Award (1980-82), and the ACS Ernest Guenther Award in the Chemistry of Essential Oils & Related Products (1988). •
Nominations sought for Morley Award The ACS Cleveland Section requests nominations for the 1990 Morley Award, presented annually to a chemist for outstanding contributions to chemistry while residing in an area within 250 miles of Cleveland. The Morley Medal and $1000 are presented at the May meeting of the Cleveland Section. Nominations should include a letter of nomination and a vita including the candidate's fields of interest, experience, awards, and most important contributions. The nomination or request for additional information should be sent to W. G. Shaw, B. P. America R&D, 9101 East Pleasant Valley Rd., Independence, Ohio 44131. The deadline for receipt of nominations is Dec. 15. •
