Carter Research Group
focused on the total synthesis of complex, biologically-active natural products
Rich Carter
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Rich Carter

Rich G. Carter

Professor of Chemistry
Tel: (541) 737-9486
Fax: (541) 737-9496
rich.carter@oregonstate.edu 		     Gilbert Hall, Rm 301
Oregon State University
Corvallis, OR 97331

Departmental Faculty Page: http://www.chemistry.oregonstate.edu/carter.html

Professional Preparation

May 1993 Gettysburg College, B.S. in Chemistry.
May 1997 University of Texas at Austin , Ph.D. in Organic Chemistry;
Professor Philip D. Magnus, Supervisor.
September 1997 - July 1999 NIH Postdoctoral Research Fellow, Oregon State University;
Professor James D. White, Supervisor.

Appointments

September 1997 -
July 1999		 NIH Postdoctoral Research Fellow, Oregon State University,
Professor James D. White, Supervisor.
August 1999 -
May 2002		 Assistant Professor of Chemistry,
University of Mississippi, Oxford, MS.
January 2000 -
May 2002		 Adjunct Assistant Professor of Medicinal Chemistry,
University of Mississippi, Oxford, MS.
June 2002 -
September 2004
 Assistant Professor of Chemistry,
Oregon State University, Corvallis, OR
September 2004 -
September 2009
 Associate Professor of Chemistry,
Oregon State University, Corvallis, OR
September 2009 -
Current
 Professor of Chemistry,
Oregon State University, Corvallis, OR

Publications

  1. 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, 6283-6306.
  2. White, J. D.; Carter, R. G.; Sundermann, K. F. "A Highly Stereoselective Synthesis of Epothilone B." J. Org. Chem. 1999, 64, 684-685.
  3. 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, 1431-1434.
  4. 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, 4367-4382.
  5. 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, 3913-3916.
  6. Carter, R. G.; Bourland, T. C. " The first vanadium-catalyzed oxidation of aryl allylic selenides with in situ [2,3] sigmatropic rearrangement." Chem. Commun. 2000, 2031-2032.
  7. 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, 5407-5413.
  8. 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, 6035-6039.
  9. White, J. D.; Carter, R. G. "Silyl Ethers." in Science of Synthesis, Ian Fleming, Ed., Thieme Publishing: Stuttgart, 2002, pp. 371-412.
  10. 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, 2177-2179. Note: Awarded "Hot Article" Status.
  11. 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, 2181-2184. Note: Awarded "Hot Article" Status.
  12. Carter, R. G.; Bourland, T. C.; Zhou, X.-T.; Gronemeyer, M. A. "Controlling Influences in Bisspiroketal Formation: Synthesis of the ABC Ring System of Azaspiracid." Tetrahedron 2003, 59, 8963-8974. Note: Invited Symposium-in-Print article.
  13. Bourland, T. C.; Carter, R. G.; Yokochi, A. F. T. "Vanadium-catalyzed selenide oxidation with in situ [2,3] sigmatropic rearrangement (SOS reaction): Scope and asymmetric applications." Org. Biomol. Chem. 2004,  2, 1315-1329.
  14. Zhang, W.; Carter, R. G.; Yokochi, A. F. T. "Unified Synthesis of C19-C26 Subunits of Amphidinolides B1, B2 and B3 by Exploiting Unexpected Stereochemical Differences in Crimmins’ and Evans’ Aldol Reactions." J. Org. Chem. 2004, 69, 2569-2572.
  15. Zhou, X.-T.; Carter, R. G. "Synthesis of the ABCD and ABCDE Ring Systems of Azaspiracid-1." Chem. Commun., 2004, 2138-2140.  Note: Issue 19 Cover Article, "Hot Paper" and Three-Page Communication.
  16. Zhang, W.; Carter. R. G. "Synthetic Studies Toward Amphidinolide B1: Synthesis of the C9-C26 Fragment." Org. Lett. 2005, 7, 4209-4212.
  17. Zhou, X.-T.; Carter, R. G. "Synthesis of the C1-C26 Northern Portion of Azaspiracid-1: Kinetic versus Thermodynamic Bisspiroketal Formation." Angew. Chem. Int. Ed. 2006, 45, 1787-1790.
  18. Ashburn, B. O.; Carter, R. G. "Diels-Alder Approach to Poly-substituted Biaryls: Rapid Entry to Tri- and Tetra-ortho-substituted Phosphorus-Containing Biaryls." Angew. Chem. Int. Ed. 2006, 45, 6737-6741.
  19. Zhou, X.-T.; Lu, L.; Furkert, D. P.; Wells, C. E.; Carter, R. G. "Synthesis of the Southern FGHI Ring System of Azaspiracid-1 and Investigation into the Controlling Elements of C28- and C36-Ketalization." Angew. Chem. Int. Ed. 2006, 45, 7622-7626.
  20. Naffziger, M. R.; Ashburn, B. O.; Perkins, J. R.; Carter, R. G. "Diels-Alder Approach for the Construction of Halogenated, ortho-Nitro Biaryl Templates and Application to the Total Synthesis of anti-HIV Agent Siamenol." J. Org. Chem. 2007, 72, 9857-9865. Note: Issue 26 Cover Article.
  21. Ashburn, B. O.; Carter, R. G.; Zakharov, L. N. "Synthesis of Tetra-ortho-Substituted, Phosphorus-Containing and Carbonyl-Containing Biaryls Utilizing a Diels-Alder Approach." J. Am. Chem. Soc. 2007, 129, 9109-9116.
  22. Ashburn, B. O.; Carter, R. G. "Diels-Alder Approach to Tetra-ortho-Substituted Biaryls Employing Propargylic Tertiary Alcohols as Dienophiles." J. Org. Chem. 2007, 72, 10220-10223.
  23. Ashburn, B. O.; Carter, R. G. "Diels–Alder approach to biaryls (DAB): Importance of the ortho-nitro moiety in the [4 + 2] cycloaddition." Org. Biomol. Chem. 2008, 6,  255-257.
  24. Ashburn, B. O; Rathbone, L. K.; Camp, E. H; Carter, R. G. "A Diels-Alder Approach to Biaryls (DAB):  Synthesis of the Western Portion of TMC-95." Tetrahedron 2008, 64, 856-865. Note: Invited Symposium-in-Print article.
  25. Yang, H.; Vasudevan, S.; Oriakhi, C. O.; Shields, J.; Carter, R. G. "Scalable Synthesis of Lissamine Rhodamine B Sulfonyl Chloride and Incorporation of Xanthene Derivatives onto Polymer Supports." Synthesis 2008, 957-961.
  26. Perkins, J. R.; Carter, R. G. "Synthesis of Programmable Tetra-ortho Substituted Biaryl Compounds Using Diels-Alder Cycloadditions / Cycloreversions of Di-Substituted Alkynyl Stannanes." J. Am. Chem. Soc. 2008, 130, 3290-3291.
  27. Carlson, E. C.; Rathbone, L. K.; Yang, H.; Collett, N. D.; Carter, R. G. "Improved Protocol for Asymmetric, Intramolecular Heteroatom Michael Addition Using Organocatalysis: Enantioselective Syntheses of Homoproline, Pelletierine and Homopipecolic Acid." J. Org. Chem. 2008, 73, 5155-5158.
  28. Lu, L.; Zhang, W.; Carter, R. G. "Total Synthesis of Cytotoxic Macrolide Amphidinolide B1 and the Proposed Structure of Amphidinolide B2." J. Am. Chem. Soc. 2008, 130, 7253-7255. Note: Three-Page Communication and Featured in Synfacts [Synfacts 2009, (5), PDF].
  29. Yang, H.; Carter, R. G.; Zakharov, L. N. "Enantioselective Total Synthesis of Lycopodine." J. Am. Chem. Soc. 2008, 130, 9238-9239. Note: Featured in Synfacts [Synfacts 2008, (7), PDF].
  30. Ashburn, B. O.; Carter, R. G.; Zakharov, L. N. "Diels-Alder Approach to Biaryls (DAB): Elucidation of Competing Tandem [2+2] Cycloaddition / [1,3] Sigmatropic Shift Pathway." J. Org. Chem. 2008, 73, 7305-7309.

  31. Yang, H. Carter, R. G. "N-(p-dodecylphenylsulfonyl)-2-Pyrrolidinecarboxamide: A Practical Proline Mimetic for Facilitating Enantioselective Aldol Reactions." Org. Lett. 2008, 10, 4649-4652.

  32. Yang, H. Carter, R. G. "Enantioselective Mannich Reactions using the Practical Proline Mimetic N-(p-dodecylphenylsulfonyl)-2-Pyrrolidinecarboxamide." J. Org. Chem. 2009, 74, 2246-4229.

  33. Yang, H. Carter, R. G. "Asymmetric Construction of Nitrogen-Containing, [2.2.2] Bicyclic Scaffolds Using N-(p-Dodecylphenylsulfonyl)-2-Pyrrolidinecarboxamide." J. Org. Chem. 2009, 74, 5151-5156. Note: Featured Article.

  34. Mahapatra, S..; Carter, R. G. "Efficient Synthesis of the C7-C20 Subunit of Amphidinolides C and F." Org. Biomol. Chem.  2009, 7, 4582-4585. Note: Hot Paper and Issue 22 Cover Article.

Patents

• White, J. D.; Carter, R. G.; Sundermann, K. F. "Method for Synthesizing Epothilones and Epothilone Analogs." U.S. Patent No. 6,596,875.

• White, J. D.; Sundermann, K. F.; Carter, R. G. "Method for Synthesizing Epothilones and Epothilone Analogs." U.S. Patent No. 6,906,188.

• White, J. D.; Carter, R. G.; Sundermann, K. F. "Method for Synthesizing Epothilones and Epothilone Analogs." U.S. Patent No. 6,598,401.

• White, J. D.; Carter, R. G.; Sundermann, K. F. "Method for Synthesizing Epothilones and Epothilone Analogs." U.S. Patent No. 7,145,018.

Honors and Service

• Glenn S. Weiland Summer Research Scholarship, 1992.

• Esther Brandt Chemistry Award, 1992.

• Stine Chemistry Prize, 1993.

• Southeastern Pennsylvania Section of the American Chemical Society Outstanding Senior Chemistry Major of Gettysburg College, 1993.

• John B. Zinn Chemistry Research Award, 1993.

• David Burton Jr. Fellowship Award, 1996.

• NIH Post-doctoral Fellow, 1998.

• Hot Article Status (2 papers) from Organic Letters, 2002.

• Consultant, Chemica Technologies, 2003-current.

• NIH NIAID Peer Review Panel for Cooperative Research for the Development of Vaccines, Adjuvants, Therapeutics, Immunotherapeutics, and Diagnostics for Biodefense, 2003.

• Invited Symposium-in-Print Articles in Tetrahedron, 2003, 2007.

• NIH Peer Review Panel, Medicinal Chemistry A (MCHA) June Study Section, Ad Hoc Reviewer, 2003-2004.

• Invited Speaker, 2004 National Science Foundation Workshop for Synthetic Organic Chemistry, Minary Center, Holderness, NH.

• Awarded Early Tenure from Oregon State University, 2004.

• Hot Paper Status from Chemical Communications, 2004.

• Inside Cover of Issue 19 from Chemical Communications, 2004.

• NIH Peer Review Panel, Chemical and Bioanalytical Sciences Fellowship Review Panel, Ad Hoc Reviewer, 2005, 2006.

• NIH Peer Review Panel, Synthetic and BIological Chemistry A (SBCA), Ad Hoc Reviewer, 2006.

• Jorunal Awardee, Synthesis / Synlett Editorial Board - Thieme Publishers, 2007.

• NIH Peer Review Panel, Synthetic and BIological Chemistry B (SBCB), Ad Hoc Reviewer, February & October 2007.

• Member, Synthetech Technology Committee, 2007-current.

• NIH Peer Review Panel, S10 Shared Instrumentation, 2007.

• Sugihara Young Faculty Research Award, 2007. 

• Cover of Issue 26 from Journal of Organic Chemistry, 2007.

• NSF Peer Review Panel, Organic & Macromolecular Chemistry Program - Synthesis, March / April 2008.

• Member, Research Corporation Awards Programs Advisory Committee, 2008 - current.

• NSF Peer Review Panel, Chemistry Research Instrumentation and Facilities: Departmental Multi-User Instrumentation (CRIF:MU), October 2008.

• NSF Peer Review Panel, Organic & Macromolecular Chemistry Program - Synthesis, October 2009.

• NIH Peer Review Panel, Synthetic and BIological Chemistry B (SBCB), Ad Hoc Reviewer, February 2010.

• Japan Society for the Promotion of Science (JSPS) Invitation Long-Term Fellowship for Research in Japan, 2010.

Financial Support

Federal Funding
• NIH R01 (GM 63723) Award Entitled "Tandem Reactions in Organic Synthesis." (April 15, 2009 - March 31, 2012).

• NSF (CHE-0848704) Award Entitled "New Methods for the Synthesis of Biaryl Templates." (July 1, 2009-June 30, 2011).

• NSF (CHE-0722319) Award Entitled "Acquisition of a 600 MHz Nuclear Magnetic Resonance Spectrometer." (September 1, 2007-August 31, 2010).

Internal Funding
• Oregon State University Venture Fund Award Entitled "Commercialization of Hua Cat for Use in Asymmetric Chemical Processes." (September 1, 2008-August 31, 2009)

Professional Societies

• Phi Beta Kappa, 1993.

• American Chemical Society, 1993.




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