RICH G. CARTER Assistant Professor of Chemistry Gilbert Hall, Room 301 Oregon State University Corvallis, OR 97331 Tel: (541) 737-9486 Fax: (541) 737-9496 E-mail: rich.carter@oregonstate.edu Web Site: http://www.onid.orst.edu/~carteric/index.html RESEARCH INTERESTS TOTAL SYNTHESIS OF BIOLOGICALLY ACTIVE COMPLEX NATURAL PRODUCTS. • Synthetic efforts toward the total synthesis of azaspiracid, a recently isolated complex spirotoxin. • Synthetic efforts toward the total synthesis of amphidinolide B1, a recently isolated cytotoxic macrolide. • Synthetic efforts toward the total synthesis of vacidin A, a promising treatment for life-threatening infections. TARGET-ORIENTED STRATEGIES FOR SOLUTION TO CURRENT SYNTHETIC PROBLEMS. • Development of the first catalytic, asymmetric method for oxidation of prochiral selenides with in situ [2,3] sigmatropic rearrangement. • Development of a tandem reaction strategies for the construction for complex diene systems. PROFESSIONAL PREPARATION September 1997 NATIONAL INSTITUTES OF HEALTH POSTDOCTORAL to June 1999 FELLOW, OREGON STATE UNIVERSITY; Professor James D. White, Supervisor. May 1997 UNIVERSITY OF TEXAS AT AUSTIN, PH.D. IN ORGANIC CHEMISTRY; Professor Philip D. Magnus, Supervisor. May 1993 GETTYSBURG COLLEGE, B.S. IN CHEMISTRY. APPOINTMENTS May 2002 to Current January 2002 to May 2002 August 1999 to May 2002 ASSISTANT PROFESSOR OF CHEMISTRY, OREGON STATE UNIVERSITY, CORVALLIS, OR. ADJUNCT ASSISTANT PROFESSOR OF MEDICINAL CHEMISTRY, UNIVERSITY OF MISSISSIPPI, OXFORD, M ASSISTANT PROFESSOR OF CHEMISTRY, UNIVERSITY OF MISSISSIPPI, OXFORD, MS. PUBLICATIONS Magnus, P.; Carter, R.; Davies, M.; Elliott, J.; Pitterna, T. "Studies on the Synthesis of the Core Structures of the Antitumor Agents Neocarzinostatin, Kedarcidin, C-1027, and Maduropeptin." Tetrahedron 1996, 52, 6283-306. White, J. D.; Carter, R. G.; Sundermann, K. F. "A Highly Stereoselective Synthesis of Epothilone B." J. Org. Chem. 1999, 64, 684-85. White, J. D.; Sundermann, K. F.; Carter, R. G. "Improved Synthesis of Epothilone B Employing Alkylation of an Alkyne for Assembly of Subunits." Org. Lett. 1999, 1, 1431-34. Carter, R.; Magnus, P.; Hodgetts, K.; McKenna, J.; Mitchell, I.; Wren., S. "Studies on the Stereoselective Synthesis of the Marine Antitumor Agent Eleutherobin." Tetrahedron 2000, 56, 4367-82. Carter, R. G.; Weldon, D. J. "Studies Directed Toward the Total Synthesis of Azaspiracid: Stereoselective Construction of C1-C12, C13-C19 and C21-C25 Fragments." Org. Lett. 2000, 2, 3913-16. Carter, R. G.; Bourland, T. C. " The first vanadium-catalyzed oxidation of aryl allylic selenides with in situ [2,3] sigmatropic rearrangement." J. Chem. Soc., Chem. Commun. 2000, 2031-32. White, J. D.; Carter, R. G.; Sundermann, K. F.; Wartmann, M. "Total Synthesis of Epothilone B, Epothilone D, and Cis and Trans 9,10-Dehydroepothilone D." J. Am. Chem. Soc. 2001, 123, 5407-13. Carter, R. G.; Graves, D. E. "Studies directed toward the total synthesis of azaspiracid. Construction of the C1-C19 carbon backbone and synthesis of the C10, C13 nonnatural transoidal bisspirocyclic ring system." Tetrahedron Lett. 2001, 42 , 6035-39. White, J. D.; Carter, R. G. "Silyl Ethers." in Science of Synthesis, Ian Fleming, Ed., Thieme Publishing: Stuttgart, 2002, pp. 371-412. Carter, R. G.; Bourland, T. C.; Graves, D. E. "1. Synthesis of ABC Ring System of Azaspiracid: Effect of D Ring Truncation on Bisspirocyclization." Org. Lett. 2002, 4, 2177-79. Note: Awarded “Hot Article” status. Carter, R. G.; Graves, D. E.; Gronemeyer, M. A., Tschumper, G. S. "2. Synthesis of ABC Ring System of Azaspiracid: A Systematic Study into the Effect of C16 and C17 Substitution on Bisspirocyclization." Org. Lett. 2002, 4, 2181-84. Note: Awarded “Hot Article” status. FINANCIAL SUPPORT NIH R01 (GM 63723) Award Entitled "Tandem Reactions in Organic Synthesis: Proposed Total Syntheses of Azaspiracid and Amphidinolide B1." (June 1, 2002 - May 31, 2007). HONORS • Hot Article Status (2 papers) from Organic Letters, 2002. • National Institutes of Health (NIH) Postdoctoral Fellow, 1998. • David Burton Jr. Fellowship Award, 1996. • Phi Beta Kappa Inductee, 1993. • John B. Zinn Chemistry Research Award, 1993. • Southeastern Pennsylvania Section of the American Chemical Society Outstanding Senior Chemistry Major of Gettysburg College, 1993. • Stine Chemistry Prize, 1993. • Esther Brandt Chemistry Award, 1992. • Glenn S. Weiland Summer Research Scholarship, 1992. PRESENTATIONS 204th American Chemical Society National Meeting, San Diego, CA. D. L. Jameson, R. G. Carter, M. D. Borden, E. P. Neuffer. "Synthesis and Coordination Chemistry of New Chiral Polypyridine Ligands." Abstract # INORG-361. 216th American Chemical Society National Meeting, Boston, MA. J. D. White, R. G. Carter, K. Sundermann "Synthetic Approach Towards the Total Synthesis of Epothilone B." Abstract # ORG-41. 2000 Joint Southeast-Southwest Regional American Chemical Society Meeting, New Orleans, LA. R. G. Carter, T. C. Bourland. "Studies Directed Towards the Vanadium-Catalyzed, Asymmetric Oxidation of Aryl, Allylic Selenides with in situ [2,3] Sigmatropic Rearrangement." Abstract # 522. 2000 Joint Southeast-Southwest Regional American Chemical Society Meeting, New Orleans, LA. D. J. Weldon, R. G. Carter. "Studies Directed toward the Total Synthesis of Azaspiracid." Abstract # 320. 221st American Chemical Society National Meeting, San Diego, CA. R. G. Carter, D. J. Weldon, T. C. Bourland. "Synthetic studies toward the total synthesis of Azaspiracid." Abstract # ORG-479. 2002 Gordon Research Conference on Natural Products, Tilton, NH. R. G. Carter, T. C. Bourland, M. A. Gronemeyer. "Progress toward the Total Synthesis of the Spirotoxin Azaspiracid." (Short Talk). INVITED SEMINARS Department of Chemistry, Colorado College (Colorado Springs, CO), "Total Synthesis of Epothilone B." November 2000. Department of Medicinal Chemistry, University of Mississippi (University, MS), "Synthetic Studies toward the Spirotoxin Azaspiracid." November 2001. Department of Chemistry, University of Memphis (Memphis, TN), "Synthetic Studies toward the Spirotoxin Azaspiracid." November 2001 Department of Chemistry, Florida State University (Tallahassee, FL), "Synthetic Studies toward the Spirotoxin Azaspiracid." November 2001 Department of Chemistry, Mississippi State University (Mississippi State, MS), "Synthetic Studies toward the Spirotoxin Azaspiracid.” February 2002 PROFESSIONAL SOCIETIES • Phi Beta Kappa, 1993. • American Chemical Society, 1993.