Carter Research Group
focused on the total synthesis of complex, biologically-active natural products
Rich Carter
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Last Updated August 2009

Publications

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

Cover Article Galley


Cover Article for Issue 22 of Organic and Biomolecular Chemistry (November 2009)
Cover Article Issue 22



The cover image depicts Battery Point Lighthouse in Crescent City, CA (photograph by Rich G. Carter) with chemical graphics of amphidinolides C/F and the synthesized C7–C20 subunit superimposed in the foreground.

See:  Org. Biomol. Chem.  2009, 7, 4582-4585. (ABSTRACT).

Part of Cover for Symposium-in-Print Series for Issue 5 of Tetrahedron (January 2008)


Tetrahedron
 "The study of aromatic compounds is one of the most fundamental areas of organic chemistry, and takes a prominent role in both undergraduate teaching and research. Classically, methods employed to make benzene derivatives have focused on electrophilic/nucleophilic substitution processes, whereas ring synthesis via condensation chemistry has been more prominent in the preparation of heteroaromatic compounds. This latter strategy holds significant advantages in the synthesis of complex and functionalised compounds because it is not restricted to generating the substitution patterns dictated by directing groups on the aromatic ring. The topic of this Symposium-in-Print aims to highlight recent achievements in this general area as it applies to benzenoid systems as well as heteroaromatics. A broad range of approaches are covered that include pericyclic, metal-mediated and metal catalysed processes. The latter theme is evident throughout this issue and highlights also the power and versatility of modern synthetic strategies such as ring closing metathesis and Au-catalysed carbon–carbon bond forming reactions. Taken together, this snapshot of benzannulation protocols provides novel routes to highly functionalised aromatic and heteroaromatic skeleta that include benzenoid compounds and pyridine derivatives, as well as indoles, pyrroles and furans." Guest Editor Joseph P. A. Harrity

See: Tetrahedron 2008, 64, 856-65 (ABSTRACT).

Cover Article for Issue 26 of the Journal of Organic Chemistry (December 2007)
JOC Cover


Halogenated, o-nitroarylalkynes (shown in the image superimposed over Yaquina Head Lighthouse, the tallest lighthouse in Oregon) react cleanly with cyclic and acyclic oxygenated dienes to generate a range of highly substituted biaryl compounds. This Diels-Alder approach to biaryls (DAB) strategy has proven useful for synthesizing a wide range of biaryl derivatives including the anti-HIV natural product siamenol.

See: J. Org. Chem. 2007, 72, 9857-75 (ABSTRACT) and J. Org. Chem. 2007, 72, 10220-23 (ABSTRACT).

Cover Article for Issue 19 of Chemical Communications (October 2004)
Cover Photo
(Cover as PDF)


The photograph (by Susan T. Carter)  shows a small collection of mussels that have been boiled and are ready to be eaten.  A bond-line image of the revised structure of azaspiracid-1, a toxin found in edible mussels, and a ball-and-stick image of the synthesized ABCDE ring system of azaspiracid-1 are overlaid on the photograph.

See: Chem. Commun. 2004, 2138-2140 (ABSRACT).

M.S. and Ph.D. Theses

1997
Rich G. Carter, Ph.D., University of Texas-Austin. Dissertation Entitled: "Part A: Studies directed toward the syntheses of the cores of Kedarcidin, Maduropeptin and C-1027; Part B: Studies directed toward the total synthesis of Eleutherobin."
Available PDF Files: Thesis

2002
T. Campbell Bourland, M.S., University of Mississippi. Thesis Entitled: "Vanadium-Catalyzed Selenide Oxidation with in situ [2,3] Sigmatropic Rearrangement: Scope and Asymmetric Applications."
Available PDF Files: Thesis

2006
Wei Zhang, Ph.D., Oregon State University. Dissertation Entitled: "Synthetic Studies toward the Total Synthesis of Amphidinolide B1."
Available PDF Files: Thesis, NMR Spectra

2008
Brad O. Ashburn, Ph.D., Oregon State University. Dissertation Entitled: "A Diels-Alder Approach to Biaryl Synthesis."
Available PDF Files: Thesis, NMR Spectra

2009
Johanna P. Schwartz, Ph.D., Oregon State University. Dissertation Entitled: "Expanding the Scope of a Diels-Alder Approach to Biaryl Synthesis."
Available PDF Files: Thesis, NMR Spectra

Liang Lu, Ph.D., Oregon State University. Dissertation Entitled: "Part I: Synthetic Studies Toward the Southern Portion of Azaspiracid-1; Part II: Total Synthesis of Amphidinolide B1 and the Proposed Structure of Amphidinolide B2."
Available PDF Files: Thesis, NMR Spectra



Patents

  1. White, J. D.; Carter, R. G.; Sundermann, K. F. "Method for Synthesizing Epothilones and Epothilone Analogs." U.S. Patent No. 6,596,875.
  2. White, J. D.; Sundermann, K. F.; Carter, R. G. "Method for Synthesizing Epothilones and Epothilone Analogs." U.S. Patent No. 6,906,188.
  3. White, J. D.; Carter, R. G.; Sundermann, K. F. "Method for Synthesizing Epothilones and Epothilone Analogs." U.S. Patent No. 6,598,401.
  4. White, J. D.; Carter, R. G.; Sundermann, K. F. "Method for Synthesizing Epothilones and Epothilone Analogs." U.S. Patent No. 7,145,018.
  5. 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.
  6. Carter, R. G.; Yang, H. "Sulfonamide-Based Organocatalysts and Methods For Their Use." Worldwide Patent Application # WO 2009/039181 A2.
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