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Carter, Rich G.

Title: Professor and Chair
Division: Organic
Research Areas: Organic
Location: LPSC 251
Phone: 541-737-9486
Fax: 541-737-9496
Email: rich.carter@oregonstate.edu

Rich CarterEducation:
B.S. Gettysburg College (1993);
Ph.D. University of Texas at Austin (1997);
NIH Postdoctoral Fellow, Oregon State University (1997-99).

Awards:
Esther Brandt Chemistry Award (1992);
Stine Chemistry Prize (1993);
John B. Zinn Chemistry Research Award (1993);
David Burton Jr. Fellowship Award (1996);
National Institutes of Health Postdoctoral Fellow (1997-99);
Awarded Early Tenure from Oregon State University (2004);
Journal Awardee, Synthesis / Synlett Editorial Board - Thieme Publishers (2007);
Sugihara Young Faculty Research Award (2007);
Research Corporation Awards Programs Advisory Committee Member (2008 - current).

Research Group Website:
http://oregonstate.edu/dept/chemistry/carter/

Organic and Bioorganic Website:
http://www.chemistry.oregonstate.edu/organic/

Research Interests

Our research efforts are focused toward the construction of structural motifs not well addressed by existing synthetic approaches.  A portion of this research is directed toward the synthesis of complex, biologically active natural products covering the spectrum in structural diversity: spiroketals, macrolides, terpenes, alkaloids and cyclic peptides.  We also are interested in developing new methods for synthesizing non-natural organic compounds.  One current area of research in this direction is the development of novel approaches for the synthesis of highly functionalized biaryl compounds.  A more detailed description of these projects can be found on our research group website.

Representative 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. Abstract
  2. White, J. D.; Carter, R. G.; Sundermann, K. F. "A Highly Stereoselective Synthesis of Epothilone B." J. Org. Chem. 1999, 64, 684-685. Abstract
  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. Abstract
  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. Abstract
  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. Abstract
  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. Abstract
  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, 5407-13. Abstract, Correction
  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. Abstract
  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.  Abstract,  PubMed Free Access
  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. Abstract,  PubMed Free Access
  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, 8963-74. Abstract,  PubMed Free Access
  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. Abstract,  PubMed Free Access
  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. Abstract,  PubMed Free Access
  15. 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
  16. Zhang, W.; Carter. R. G. "Synthetic Studies Toward Amphidinolide B1: Synthesis of the C9-C26 Fragment." Org. Lett. 2005, 7, 4209-4212.  Abstract,   PubMed Free Access
  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. Abstract,  PubMed Free Access
  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. Abstract
  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. Abstract, Correction,  PubMed Free Access
  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. Abstract
  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. Abstract
  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. Abstract
  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. Abstract
  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. Abstract
  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. Abstract
  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.  Abstract
  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.  Abstract
  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.  Abstract, Correction, PubMed Free Access
  29. Yang, H.; Carter, R. G.; Zakharov, L. N. "Enantioselective Total Synthesis of Lycopodine." J. Am. Chem. Soc. 2008,130, 9238-9239. Abstract, PubMed Free Access
  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. Abstract
  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. Abstract
  32. Yang, H. Carter, R. G. "Enantioselective Mannich Reactions using the Practical Proline Mimetic N-(p-dodecylphenylsulfonyl)-2-Pyrrolidinecarboxamide." J. Org. Chem. 2009, 74, 2246-2249. Abstract
  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. Abstract
  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.  Abstract
  35. Yang, H.; Carter, R. G. "Organocatalyzed, enantioselective synthesis of bicyclo- [2.2.2]-octanes containing benzylic, all-carbonquaternary centers." Tetrahedron 2010, 66, 4854-4859. Abstract
  36. 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
  37. 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
  38. Carter, R. G.; Kuiper, D. L. "2.18 Product Class 18: Spiroketals, Bisspiroketals and Spiroaminals" Stereoselective Synthesis, in press.
  39. Collett, N. D.; Carter, R. G. "News and Views: Moving backwards in new ways." Nature Chem. 2010, 2, 613-614. Abstract
  40. 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. Chem. 2010, 75, 7279-7290.  Abstract
  41. Yang, H.; Carter, R. G. "Invited Account: Proline Sulfonamides: Better Late than Never." Synlett 2010, 2827-2838.  Abstract