Qualifications and Experience
Eric D. Edstrom, Ph.D.
Organic Geochemistry
EDUCATION
1987 Ph.D., Organic Chemistry, University of Minnesota, Minneapolis, Minnesota. Advisor: Professor Tom Livinghouse
Thesis Title: Carbocycle Annulation Mediated by Episulfonium and Episelenonium Ions.
1983 Bachelors of Science (cum laude), Chemistry, Fort Lewis College, Durango, ColoradoEXPERIENCE
1996-present Assistant Professor of Chemistry, Department of Chemistry, University of Montana, Missoula, MT
1989-1996 Assistant Professor of Chemistry, Department of Chemistry and Biochemistry, Utah State University, Logan, Utah
1987-1989 Postdoctoral Research Fellow, Stanford University, Stanford, California. Advisor: Professor Barry M. Trost
1983-1985 Teaching Assistant, University of Minnesota
PUBLICATIONS
1. "Biomimetic Total Synthesis of (-) Codeine." James D. White, Giargio Caravatti, Toni B. Kline, Eric Edstrom, Kenner C. Rice, and Arnold Brossi Tetrahedron, 1983, 39, 2393.
2. "An Expedient Approach to Carbocycle Annulation Via Silver Ion Assisted Episulphonium Ion Cyclizations." Eric D. Edstrom and Tom Livinghouse J. Chem. Soc. Chem. Comm., 1986, 279.
3. "New Methods for the Generation of Episulfonium Ions. An Application to the Synthesis of Carbocycles via Sulfenium Ion Promoted Arene-Alkene Cyclizations." Eric D. Edstrom and Tom Livinghouse J. Am. Chem. Soc., 1986, 108, 1334.
4. "On the Direct Generation of Episelenonium Ions from Alkenes. An Efficient New Procedure for Effecting Selenylative Arene-Alkene Carboannulations." Eric D. Edstrom and Tom Livinghouse Tetrahedron Letters, 1986, 3483.
5. "On the Direct Generation of Episulfonium Ions from Alkenes. An Application to the Synthesis of Higher Order Carbocycles via Episulfonium Ion Mediated Polyene Cyclizations." Eric D. Edstrom and Tom Livinghouse J. Org. Chem. 1987, 52, 949.
6. "A Cycloisomerization Approach to Tetrahydrofurans." Barry M. Trost, Eric D. Edstrom, and Mary Beth Carter-Petillo J. Org. Chem. 1989, 54, 4489.
7. "A Metal Catalyzed Approach to (±)-Phyllanthocin." Barry M. Trost and Eric D. Edstrom Angew Chem Int. Ed. Engl. 1990, 29, 520.
Papers Since Starting Independant Career
8. "Photoreactions of 6-(1'-Triazolyl)uracils. Synthesis of 7,8-Disubstituted Pyrrolo[2,3-d]pyrimidines and Pyrimido[4,5-c]isoquinolines" Eric D. Edstrom and Wei Yuan Tetrahedron Lett. 1991, 323.
9. "New Methodology for the Synthesis of Indolizidine and Quinolizidine Ring Systems." Eric D. Edstrom J. Am. Chem. Soc. 1991, 113, 6690.
10. "An Unexpected Reversal in the Stereochemistry of Transannular Cyclizations. A Stereoselective Synthesis of (±)-Epilupinine." Eric D. Edstrom Tetrahedron Lett. 1991, 5709.
11. "Synthesis of a Novel Pyrrolo[2,3-d]pyrimidine Alkaloid, Rigidin." Eric D. Edstrom and Yuan Wei J. Org. Chem. 1993, 58, 403.
12. "Cyclization of 5-(Carboxymethylamino)-pyrimidines. Synthesis and Characterization of Novel Imidazolo[1,2-c]pyrimidines." Eric D. Edstrom, Yuan Wei, and Michelle Gordon J. Org. Chem. 1994, 59, 2473.
13. Cyclodehydration of 4-Carboxymethylaminopyridin-2-ones. A New, Efficient Synthesis of Pyrrolo[3,2-c]pyridin-4-ones and Pyrido[3,4-b]pyrrololizidi-1-ones." Eric D. Edstrom and Tao Yu Tetrahedron Lett. 1994, 35, 6985.
14. A New Efficient Route to -2’-Deoxyribosyl-5-Substituted Pyrrolo[2,3- d]pyrimidines. Palladium Catalyzed Functionalizations of a C-5 Triflate Intermediate." Eric D. Edstrom and Yuan Wei J. Org. Chem. 1994, 59, 6902.
15. Total Synthesis of 2’-Deoxycadeguomycin, a New Pyrrolo[2,3-d]pyrimidine Nucleotide Analogue. Eric D. Edstrom and Yuan Wei Tetrahedron Lett. 1994, 35, 8989.
16. Synthesis of 4-Hydroxy-3-Substituted Indoles and Indolequinones via an 3- Acetyloxy-4-oxo-4,5,6,7-tetrahydroindole Intermediate." Eric D. Edstrom SynLett, 1995, 49.
17. A New Efficient Route to -2’-Deoxyribosyl-5-Substituted Pyrrolo[2,3- d]pyrimidines. Total Synthesis of 2-Deoxycadeguomycin." Eric D. Edstrom and Yuan Wei J. Org. Chem. 1995, 60, 5069.
18. Ionization of Pyrido[3,4-b]pyrrolizidine and Pyrrolo[1,2-a]indole Triflate Derivatives. A Novel Approach to the Mitosene Skeleton." Eric D. Edstrom and Tao Yu J. Org. Chem. 1995, 60, 5382.
19. Regioselective Oxidative of 1,2,5,6,7,8-Hexahydro-8-oxo-1H-pyrrolo[1,2- a]indoles. Useful Intermediates for the Synthesis of Mitosenes. Eric D. Edstrom, Tao Yu, and Zachary Jones Tetrahedron Lett. 1995, 36, 7035.
20. Regioselective Oxidative Amination of 3-Carbomethoxyindole-4,7-quinones." Eric D. Edstrom and Zachary Jones Tetrahedron Lett. 1995, 36, 7039.
21. Use of Methylthiomethyl (MTM) for N1 protection in Pyrrolo[2,3-d]pyrimidi- 2,4-diones." Eric D. Edstrom and Xianqi Feng, Tetrahedron Lett. 1996, 37, 759.
22. A Highly Efficient Synthesis of a Fully Functionalized Azirodinomitosene." Eric D. Edstrom and Tao Yu, Tetrahedron 1997, 53, 4549.
23. o-Nitrobenzyl as a Photocleavable Nitrogen-Protecting Group for Indoles, Benzimdazole, and 6-Chlorouracil." Troy Voelker, Tim Ewell, Jean Joo, and Eric D. Edstrom Tetrahedron Lett. 1998, 35, 359.
Book Chapters
"Episulfonium Ions and Episelenoium Ions. Versatile Heterocyclic Cations for the Synthesis of Natural Products." Scott R. Herring, Eric D. Edstrom and Tom Livinghouse Advances in Heterocyclic Natural Product Synthesis, W. H. Pearson, Ed. 1992, 2, 299.
Synthesis of [b]-Annelated Pyrroles via an Acylation Approach." Eric D. Edstrom Advances in Nitrogen Heterocycles, C. Moody,Ed. 1998, in press.
AWARDS AND HONORS
Faculty Recognition Award in Chemistry, 1980-81, Fort Lewis College
National Science Foundation Undergraduate Summer Research Fellowship, 1981, Oregon State University; Corvallis, Oregon
Proctor and Gamble Fellowship, 1984-85, Department of Chemistry, University of Minnesota
Lee Irwin Smith Award in Organic Chemistry, 1986, University of Minnesota
American Cancer Society Jr. Faculty Research Award, 1993-96, Utah State University
PROFESSIONAL SOCIETIES
American Chemical Society, Organic and Medicinal Chemistry Divisions
International Society of Heterocyclic Chemistry
PROFESSIONAL SERVICE
1990- Reviewer for Journal of Organic Chemistry, Journal of the American Chemical Society, Tetrahedron, Tetrahedron Letters, Chemical Reviews
1992- Grant Reviewer for National Science Foundation, ACS Petroleum Research Fund
RECENT INVITED TALKS AND LECTURES
Problems with Chemical Evolution from the Prespective of an Organic Chemist" Department of Chemistry, Southern Adventist University, Collegedale, TN, April 17, 1998.
New Directions for the Development of Synthetic Methodologies." Department of Chemistry, Montana Tech, Butte, MT, March 28, 1997.
A Centralized Strategy for the Construction of Pyrrole Containing Molecules." Department of Chemistry, Princeton University, Princeton NJ, December 15, 1995.
A Centralized Strategy for the Construction of Pyrrole Containing Molecules." FMC Corporation, Princeton NJ, December 13, 1995.
A Centralized Strategy for the Construction of Pyrrole Containing Molecules." Department of Chemistry, Rutgers University, New Brunswick, NJ, December 12, 1995.
A Multidimentional Strategy for the Synthesis of Pyrrole Containing Molecules." Department of Chemistry and Biochemistry, Montana State University, Bozeman, March 3, 1995.
"Synthesis of Pyrrole Containing Molecules." Discovery and Process Research, Eli Lilly and Co., Indianapolis, IN, August 8, 1994.
"Annulation of Pyrrole Rings Onto Six-Membered Rings." Gordon Research Conference on Heterocyclic Compounds, New Hampton School, NH July 10-15, 1994.
"Synthesis of Pyrrole Annulated Heterocycles." Department of Chemistry and Biochemistry, University of California, Santa Cruz, April 18, 1994.
Expeditious New Routes to Heterocyclic Structures." Department of Chemistry, University of California, Riverside, April 15, 1994.
"Annulation of Pyrrole Rings Onto Six-Membered Rings." Department of Chemistry and Biochemistry, Brigham Young University, April 4, 1994.
"Annulation of Pyrrole Rings Onto Six-Membered Rings." Department of Chemistry, University of Utah, March 3, 1994.
MEETINGS AND PRESENTATIONS
"Boll Weevil Pheromone Synthesis." William R. Bartlett*, Eric D. Edstrom, and Chris Switzer, American Association for the Advancement of Science Regional Meeting, El Paso, TX, April 17-19, 1982.
A New and Efficient Method for the Synthesis of Tetralin Derivatives via Episulfonium Ion Cyclizations." Eric E. Edstrom and Tom Livinghouse*, 190th ACS National Meeting, Chicago, IL, Sept 8-13, 1985 (talk).
Episelenonium Ion Mediated Carboannulations of Arene-Alkenes." Eric E. Edstrom and Tom Livinghouse*, 192nd ACS National Meeting, Anaheim, CA, Sept 7-12, 1986 (talk).
Synthesis of 7-Deazapurine Base Analogues." Eric D. Edstrom* and Yuan Wei, 45th/19th Joint NorthWest/Rocky Mtn. Regional Meeting, Salt Lake City, UT, June 13-15, 1990 (talk).
A New Approach for the Synthesis of Indolizidine Alkaloids." Gordon Research Conference on Heterocyclic Compounds, New Hampton School, NH, July 9-13, 1990 (poster).
"New Methodology for the Synthesis of Indolizidine and Quinolizidine Alkaloids." Eric D. Edstrom, 201st ACS National Meeting , Atlanta, Georgia, April 4-19, 1991 (poster for Organic Division and Sci-Mix).
"Annulation of Pyrrole Rings Onto Six-Membered Rings." Eric D. Edstrom* and Yuan Wei, 13th International Congress of Heterocyclic Chemistry, Corvallis, Oregon, August 11-16, 1991 (poster).
"Annulation of Pyrrole Rings Onto Six-Membered Rings." Eric D. Edstrom* and Yuan Wei, 203rd ACS National Meeting, San Francisco, CA, April 5-10, 1992 (talk).
"Annulation of Pyrrole Rings Onto Six-Membered Rings. Total Synthesis of Rigidin." Eric D. Edstrom and Yuan Wei, Gordon Research Conference on Heterocyclic Compounds, New Hampton School, NH July 6-10, 1992 (poster).
"Synthesis of the Novel Pyrrolo[2,3-d]pyrimidine Alkaloid, Rigidin" Eric D. Edstrom* and Yuan Wei, 205th ACS National Meeting, Denver, CO, March 28-April 2, 1993 (talk).
"New Methodology for the Synthesis of Pyrrolo[2,3-d]pyrimidine Nucleotide Analogues." Eric D. Edstrom* and Yuan Wei, 33rd National Organic Symposium, Bozeman, MT, June 13-17, 1993 (poster).
"New Methodology for the Synthesis of Pyrrolo[2,3-d]pyrimidine Nucleotide Analogues." Eric D. Edstrom and Yuan Wei, Gordon Research Conference on Purines, Pyrimidines, and Related Substances, Salve Regina University, Newport, RI, July 5-9, 1993 (poster).
"Cyclodehydrations of Carboxymethylamino-Substituted 2-H-Pyridones and Pyrimidones." Eric D. Edstrom, Yuan Wei, and Tao Yu, 207th ACS National Meeting, San Diego, CA, March 13-18, 1994 (talk).
"Annulation of Pyrrole Rings Onto Six-Membered Rings." Eric D. Edstrom, Gordon Research Conference on Heterocyclic Compounds, New Hampton School, NH July 10-15, 1994 (talk).
Solvolysis of Pyrrole-3-Triflates to 2-Substituted-3-Ketopyrroles." Eric D. Edstrom* and Tao Yu, 209th ACS National Meeting, Anaheim, CA, April 2-6, 1995 (talk).
Oxidation Pathways for 1,2,5,6,7,8-Hexahydro-8-oxo-1H-pyrrolo[1,2-a]indoles. Versitile Intermediates for the Synthesis of Mitosenes." Eric D. Edstrom, Tao Yu, and Zachary Jones, 50th/12th Joint NorthWest/Rocky Mtn. Regional Meeting, Park City, UT, June 14-17, 1995 (talk).
Regioselective Oxidative Amination of Indolequinones." Eric D. Edstrom and Zachary Jones, 50th/12th Joint NorthWest/Rocky Mtn. Regional Meeting, Park City, UT, June 14-17, 1995 (talk).
Ionization of Pyrrole-3-triflates to 2-Substituted 3-Ketopyrroles." Eric D. Edstrom and Tao Yu, 50th/12th Joint NorthWest/Rocky Mtn. Regional Meeting, Park City, UT, June 14-17, 1995 (talk).
o-Nitrobenzyl as a Photocleavable Nitrogen-Protecting Group for Indoles." Eric D. Edstrom, Troy Voelker, and Tim Ewell, 50th/12th Joint NorthWest/Rocky Mtn. Regional Meeting, Park City, UT, June 14-17, 1995 (poster).
"A New Approach for the Synthesis of Mitosenes." Gordon Research Conference on Heterocyclic Compounds, New Hampton School, NH July 9-12, 1995 (poster).
Progress on the Total Synthesis of Aziridinomitosenes." Eric D. Edstrom and Tao Yu, 211th ACS National Meeting, San Diego, CA, March 24-28, 1996 (talk).
Oxidative Amination of Indole-4,7-quinones. Synthesis of the Soil Metabolite BE-10988." Eric D. Edstrom and Zachary Jones, 211th ACS National Meeting, San Diego, CA, March 24-28, 1996 (poster).
Chemistry of Novel Cyclic C-Acyl Imiminum Ions." Gordon Research Conference on Heterocyclic Compounds, Newport, RI. June 29 - July 4, 1997 (poster).
Chemistry of Novel Cyclic C-Acyl Imiminum Ions." 16th International Congress of Heterocyclic Chemistry, Montana State University, Bozeman, MT. August 10 - 15, 1997 (talk).