OREGON STATE UNIVERSITY

About Rich Carter


Professor and Chair

Department of Chemistry

Email: rich.carter@oregonstate.edu

Twitter: @richgcarter_OSU or http://www.twitter.com/richgcarter_OSU

Fax: 541-737-2062

Faculty Office Contact Information: Chair's Office Contact Information: Mailing Address:

Linus Pauling Science Center

Room 251

Tel: 541-737-9486

Gilbert Hall

Room 153

Tel: 541-737-6700

Chemistry Department

153 Gilbert Hall

Oregon State University

Corvallis, OR 97331

Professional Preparation

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

Appointments

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
January 2012 - 
Current
Chair - Department of Chemistry,
Oregon State University, Corvallis, OR

July 2012 - 
Current

Co-founder and CEO
Valliscor, LLC Corvallis, OR

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 199652, 6283-6306. Abstract
  • White, J. D.; Carter, R. G.; Sundermann, K. F. "A Highly Stereoselective Synthesis of Epothilone B." J. Org. Chem. 199964, 684-685. Abstract
  • 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. 19991, 1431-1434. Abstract
  • Carter, R.; Magnus, P.; Hodgetts, K.; McKenna, J.; Mitchell, I.; Wren., S. "Studies on the Stereoselective Synthesis of the Marine Antitumor Agent Eleutherobin."Tetrahedron 200056, 4367-4382. Abstract
  • 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. 20002, 3913-3916. Abstract
  • 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. Abstract
  • 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. 2001123, 5407-13. AbstractCorrection
  • 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. 200142, 6035-6039. Abstract
  • 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, 2177-2179.  Abstract,  PubMed Free Access 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 C17Substitution on Bisspirocyclization." Org. Lett. 20024, 2181-2184. Abstract,  PubMed Free Access Note: Awarded "Hot Article" Status
  • 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 200359, 8963-74Abstract,  PubMed Free Access Note: Invited Symposium-in-Print article
  • 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. Abstract,  PubMed Free Access
  • 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. Abstract,  PubMed Free Access
  • Zhou, X.-T.; Carter, R. G. "Synthesis of the ABCD and ABCDE Ring Systems of Azaspiracid-1." Chem. Commun. 2004, 2138-2140 Abstract,  PubMed Free Access Note: Issue 19 Cover Article, "Hot Paper" and Three-Page Communication.
  • Zhang, W.; Carter. R. G. "Synthetic Studies Toward Amphidinolide B1: Synthesis of the C9-C26 Fragment." Org. Lett. 20057, 4209-4212.  Abstract,   PubMed Free Access
  • 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.200645, 1787-1790. Abstract,  PubMed Free Access
  • 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. 200645, 6737-6741. Abstract
  • 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. 200645, 7622-7626. AbstractCorrection,  PubMed Free Access
  • 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. Abstract Note: Issue 26 Cover Article
  • 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. 2007129, 9109-9116. Abstract
  • 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. Abstract
  • 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. 20086,  255-257. Abstract
  • 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 200864, 856-865Abstract Note: Invited Symposium-in-Print article
  • 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. Abstract
  • 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.  Abstract
  • 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. 200873, 5155-5158.  Abstract
  • 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. 2008130, 7253-7255.  AbstractCorrectionPubMed Free Access Note: Three-Page Communication and Featured in Synfacts [Synfacts 2009, (5), 474 PDF]. 
  • Yang, H.; Carter, R. G.; Zakharov, L. N. "Enantioselective Total Synthesis of Lycopodine." J. Am. Chem. Soc. 2008,130, 9238-9239. AbstractPubMed Free Access Note: Featured in Synfacts [Synfacts 2008, (1), 7  PDF].
  • 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. 200873, 7305-7309. Abstract
  • Yang, H. Carter, R. G. "N-(p-dodecylphenylsulfonyl)-2-Pyrrolidinecarboxamide: A Practical Proline Mimetic for Facilitating Enantioselective Aldol Reactions." Org. Lett. 200810, 4649-4652. Abstract PubMed Free Access
  • Yang, H. Carter, R. G. "Enantioselective Mannich Reactions using the Practical Proline Mimetic N-(p-dodecylphenylsulfonyl)-2-Pyrrolidinecarboxamide." J. Org. Chem. 200974, 2246-2249. Abstract
  • Yang, H. Carter, R. G. "Asymmetric Construction of Nitrogen-Containing, [2.2.2] Bicyclic Scaffolds Using N-(p-Dodecylphenylsulfonyl)-2-Pyrrolidinecarboxamide." J. Org. Chem. 200974, 5151-5156. Abstract Note: Featured Article
  • Mahapatra, S.; Carter, R. G. "Efficient Synthesis of the C7-C20 Subunit of Amphidinolides C and F." Org. Biomol. Chem. 20097, 4582-4585.  Abstract Note: Hot Paper and Issue 22 Cover Article  PubMed Free Access
  • Yang, H.; Carter, R. G. "Organocatalyzed, enantioselective synthesis of bicyclo- [2.2.2]-octanes containing benzylic, all-carbonquaternary centers." Tetrahedron 201066,4854-4859Abstract Note: Invited Symposium-in-Print article 
  • Yang, H.; Carter, R. G. "Synthesis of All-Carbon, Quaternary Center-Containing Cyclohexenones through an Organocatalyzed, Multi-Component Coupling." Org. Lett. 2010, 12, 3108-3111. Abstract  Note: Featured in Synfacts [Synfacts 2010 (8), 944 PDF].
  • Yang, H.; Carter, R. G. "Development of an Enantioselective Route towards the Lycopodium Alkaloids: Total Synthesis of Lycopodine." J. Org. Chem. 2010, 75, 4929-4938.  Abstract Note: Featured Article PubMed Free Access
  • Carter, R. G.; Kuiper, D. L. "2.18 Product Class 18: Spiroketals, Bisspiroketals and Spiroaminals" Stereoselective Synthesis, 2010, Volume 2, 863-914.
  • Collett, N. D.; Carter, R. G. "News and Views: Moving backwards in new ways." Nature Chem. 20102, 613-614. Abstract
  • Yang, H.; Mahapatra, S.; Cheong, P. Y.-H.; Carter, R. G. "Highly Stereoselective and Scalable anti-Aldol Reactions using N-(p-dodecylphenylsulfonyl)-2-Pyrrolidinecarboxamide: Scope and Origins of Stereoselectivities."  J. Org. Chem201075, 7279-7290.  Abstract PubMed Free Access
  • Yang, H.; Carter, R. G. "Invited Account: Proline Sulfonamides: Better Late than Never." Synlett 2010, 2827-2838.  Abstract Note: Invited Account PubMed Free Access
  • Harada, K.; Imai, A.; Uto, K.; Carter, R. G.; Kubo, M.; Hioki, H.; Fukuyama, Y. "Synthesis of the ABC Ring System of Jiadifenin via Pd-Catalyzed Cyclizations." Org. Lett. 201113, 988-991Abstract
  • Harada, K.; Horiuchi, H.; Tanabe, K.; Carter, R. G.; Esumi, T.; Kubo, M.; Hioki, H.; Fukuyama, Y. "Asymmetric synthesis of (-)-chicanine using a highly regioselective intramolecular Mitsunobu reaction and revision of its absolute configuration." Tetrahedron Lett. 201152, 3005-3008. Abstract
  • Collett, N. D.; Carter, R. G. "Stereoselective Synthesis of the Eastern Quinolizidine Portion of Himeradine A." Org. Lett. 201113, 4144-4147. Abstract PubMed Free Access
  • McIntosh, M. L.; Johnston, R. C.; Pattawong, O.; Ashburn, B. O.; Naffziger, M. R.; Cheong, P. H.-Y.; Carter, R. G. "Synthesis and Computational Analysis of Densely Functionalized Triazoles Using o-Nitrophenylalkynes."  J. Org. Chem. 2012, 77, 1101-1112. Abstract
  • Veerasamy, N.; Carlson, E. C.; Carter, R. G. "Expedient Enantioselective Synthesis of Cermizine D." Org. Lett. 201214, 1596-1599. Abstract 
  • Yang, H., Banerjee, S.; Carter, R. G. "Proline Sulphonamide-Catalysed Yamada-Otani Condensation: Reaction Development, Substrate Scope and Scaffold Reactivity."Org. Biomol. Chem. 201210, 4851-4863. Abstract Note: Invited Web-Themed Issue on Organocatalysis and Issue 25 Cover Article  
  • Pierce, M.; Johnston, R. C.; Mahapatra, S.; Yang, H.; Carter, R. G.; Cheong, P. H.-Y. "The Mechanism and Stereoselectivity of a Dual Amino-Catalyzed Robinson Annulation: Rare Duumvirate Stereocontrol." J. Am. Chem. Soc. 2012134, 13624–13631. Abstract 
  • Kang, J. Y.; Carter, R. G. "Primary Amine, Thiourea-Based Dual Catalysis Motif for Synthesis of Stereogenic, All-Carbon Quaternary Center-Containing Cycloalkanones."Org. Lett. 201214, 3178-3181. Abstract 
  • Mahapatra, S.; Carter, R. G. “Enantioselective Total Synthesis of Amphidinolide F.” Angew. Chem. Int. Ed. 201251, 7948-7951.  Abstract Note: Awarded "Hot Paper" status and Issue 32 Cover Article  
  • McIntosh, M. L.; Naffizger, M. R. Ashburn, B. O.; Zakharov, L. N.; Carter, R. G. "Highly regioselective nitrile oxide dipolar cycloadditions with ortho-nitrophenyl alkynes." Org. Biomol. Chem. 201210, 9204-9213.  Abstract
  • Saha, M.; Carter, R. G. "Toward a Unified Approach for the Lycopodines: Synthesis of 10-Hydroxylycopodine, Deacetylpaniculine and Paniculine." Org. Lett201315, 736-739. Abstract
  • Lu, L.; Zhang, W.; Nam, S.; Horne, D. A.; Jove, R.; Carter, R. G. "Amphidinolide B: Total Synthesis, Structural Investigation and Biological Evaluation." J. Org. Chem.201378, 2213–2247. Abstract Note: Featured Article
  • Veerasamy, N.; Carlson, E. C.; Collett, N. D.; Saha, M.; Carter, R. G. "Enantioselective Approach to Quinolizidines: Total Synthesis of Cermizine D and Formal Syntheses of Senepodine G and Cermizine C" J. Org. Chem. 201378, 4779-4800. Abstract
  • Mahapatra, S.; Carter, R. G. “Exploiting Hidden Symmetry in Natural Products: Total Syntheses of Amphidinolides C and F.” J. Am. Chem. Soc. 2013135, 10792-10803. Abstract
  • 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.
  • Carter, R. G.; Ashburn, B. O.; Naffziger, M. R.; Schwartz, J. P. "Method for Making Biaryl Compounds,Compounds Made by the Method, and Method for their Use." Worldwide Patent Application # WO 2008/156656 A2.
  • Carter, R. G.; Yang, H. "Sulfonamide-Based Organocatalysts and Methods For Their Use." Worldwide Patent Application # WO 2009/039181 A2.
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, 2010.
  • 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 - 2012.
  • 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.
  • Inside Cover of Issue 22 from Organic and Biomolecular Chemistry Communications, 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.
  • Visiting Professor, Tokushima Burni University, 2010.
  • NSF Peer Review Panel, Chemical Synthesis Panel, March 2011.
  • NIH Peer Review Panel, Synthetic and BIological Chemistry A (SBCA), Ad Hoc Reviewer, June 2011.
  • Chair - Department of Chemistry, Oregon State University, January 2012 - current.

Financial Support

Federal Support

  • NIH R01 (GM 63723) Award Entitled "Tandem Reactions in Organic Synthesis." 
  • NSF (CHE-0549884, CHE-0848704) Award Entitled "New Methods for the Synthesis of Biaryl Templates."
Foundation Support
  • M. J. Murdock Charitable Trust (2005265) Award Entitled “Acquisition of a High Field Nuclear Magnetic Resonance Spectrometer.” 
  • Research Corporation (unrestricted gift).
  • Oregon Nanoscience and Microtechnologies Institute (ONAMI) GAP award.
Other Support
  • Synthetech, Inc.
  • Japanese Society for the Promotion of Science
  • Hewlett-Packard Corporation
  • Oregon State University

Professional Societies

  • Phi Beta Kappa, 1993.
  • American Chemical Society, 1993.