Publications

  1. Huynh, U.; Lim, D.; Uddin, M. D.; Wengryniuk, S. E.; McDonald, S. L; Dey, S.; Coltart, D. M. "Formation, Alkylation and Hydrolysis of Chiral Nonracemic N-Amino Cyclic Carbamate Hydrazones: A Highly Effective Approach to the Enantioselective a-Alkylation of Ketones" J. Org. Chem. 2018 (in press).

    • Selected as a feature article.
  2. Rastelli, E. J.; Coltart, D. M. "A Stereodivergent Synthesis of b,g-Fused Bicyclic g-Lactones via a Multicomponent Ring Expansion Cascade" Chem 2018 (Published 8/23/2028 – DOI:https://doi.org/10.1016/j.chempr.2018.08.007).

  3. Uddin, M. D.; Coltart, D. M. "Mismatch-Free Double Asymmetric Induction Strategy for the Alkylation of Chiral Nonracemic Methyl Ketones" Org. Lett. 2018, 20, 3723–3727.

    • Featured in Synfact, 2018, 970.
  4. Rastelli, E. J.; Coltart, D. M. " Synthesis and Biological Activity of Apratoxin Derivatives " Tetrahedron 2017, 74, 2269–2290.
  5. Alfie, R. J.; Truong, N.; Yost, J. M.; Coltart, D. M. "A Kinetically Controlled Direct Aldol Addition of a-Chloro Thioesters via Soft Enolization" Tetrahedron Lett. 2017, 58, 185–189.
  6. Rastelli, E. J.; Truong, N.; Coltart, D. M. "Asymmetric Induction in Hydroacylation by Cooperative Iminium Ion-Transition Metal Catalysis" Org. Lett. 2016, 18, 5588–5591.
  7. Huynh, U.; Uddin, M. D.; Wengryniuk, S. E.; McDonald, S. L; Coltart, D. M. "On the Regioselectivity, Diasteroselectivity and Hydrolysis in ACC Hydrazone Alkylation" Tetrahedron 2017, 73, 432–436.
  8. Huynh, U.; Uddin, M. D.; Wengryniuk, S. E.; McDonald, S. L; Coltart, D. M. "A Simple and Efficient Approach to the N-Amination of Oxazolidinones Using Monochloroamine" Tetrahedron Lett. 2016 57, 4799–4802.
  9. Rastelli, E. J.; Coltart, D. M. "Asymmetric Synthesis of (+)-anti- and (–)-syn-Mefloquine Hydrochloride" J. Org. Chem. 2016, 81, 9567–9575.
  10. Truong, N.; Sauer, S. J.; Seraphin-Hatcher, C.; Coltart, D. M. "Direct Carbon–Carbon Bond Formation via Reductive Soft Enolization: A syn-Selective Mannich Addition of α-Iodo Thioesters" Org. Biomol. Chem. 2016, 14, 7864–7868.

  11. Uteuliyev, M. M.; Nguyen, T. T.; Coltart, D. M. "Diastereoselective addition of Grignard reagents to a-epoxy N-sulfonyl hydrazones" Nature Chem. 2015, 7, 1024–1027.

    • Selected as "Synfact of the Month", Synfacts, 2016, 71.
    Featured in Synform, 2016, A40–A41.

  12. Rastelli, E. J.; Coltart, D. M. "A Concise and Highly Enantioselective Total Synthesis of (+)-anti- and (–)-syn-Mefloquine Hydrochloride: Definitive Absolute Stereochemical Assignment of the Mefloquines" Angew. Chem. Int. Ed. 2015, 127, 14276–14280.

    • Selected as a "Hot Paper".
  13. Tarsis, E. M.; Rastelli, E. J.; Wengryniuk, S. E.; Coltart, D. M. "The Apratoxin Marine Natural Products: Isolation, Structure Determination, and Asymmetric Total Synthesis" Tetrahedron 2015, 71, 5029–5044.
  14. Dey, S.; Wengryniuk, S. E.; Tarsis, E. M.; Robertson, B. R.; Zhou, G.; Coltart, D. M. "A Formal Asymmetric Synthesis of Apratoxin D via Advanced-Stage Asymmetric ACC α,α-Bisalkylation of a Chiral Nonracemic Ketone" Tetrahedron Lett. 2015, 56, 2927–2929.

  15. Garnsey, M. R.; Uteuliyev, M.; Coltart, D. M. "Asymmetric Synthesis of Structural Analogues of (+)-Clusianone via Enantioselective ACC Alkylation" Tetrahedron Lett. 2015, 56, 3183–3185.

    • Invited submission to Harry Wasserman Memorial Issue.
  16. Knight, J. D.; Coltart, D. M. "Expanding the Scope of the Asymmetric Anti-Aldol Addition of Chiral N-Amino Cyclic Carbamate Hydrazones" Tetrahedron Lett. 2013, 54, 5470–5472.
  17. Knight, J. D.; Coltart, D. M. "Asymmetric Anti-Aldol Addition of Achiral Ketones via Chiral N-Amino Cyclic Carbamate Hydrazones" Chem. Commun. 2013, 49, 7495–7497.
  18. Robertson, B. D.; Wengryniuk, S. E.; Coltart, D. M. "Asymmetric Total Synthesis of Apratoxin D" Org. Lett. 2012, 14, 5192–5195.

  19. Hatcher, J. M.; Kohler, M. C.; Coltart, D. M. "Catalytic Asymmetric Addition of Thiols to Nitrosoalkenes: An Umpolung Strategy for the Synthesis of Chiral Non-Racemic α-Sulfenyl Ketones" Org. Lett. 2011, 13, 3810–3813.
    Featured in Synfacts, 2011, 1012.

  20. Knight, J. D.; Sauer, S. J.; Coltart, D. M. "Asymmetric Total Synthesis of the Anti-Malarial Drug (+)-Mefloquine Hydrochloride via Chiral N-Amino Cyclic Carbamate Hydrazones" Org. Lett. 2011, 13, 3118–3121.

    Featured in Synfact, 2011, 935.

  21. Wengryniuk, S. E.; Lim, D.; Coltart, D. M. "Regioselective Asymmetric α,α-Bisalkylation of Ketones via Complex Induced Syn-Deprotonation" J. Am. Chem. Soc. 2011, 133, 8714–8720.

    • Highlighted in: Enantioselective Construction of Alkylated Centers, Organic Chemistry Portal, February 2012.
  22. Garnsey, M. R.; Matous, J. A.; Kwiek, J. J.; Coltart, D. M. "Asymmetric Total Synthesis of (+)- and (–)-Clusianone and (+)- and (–)-Clusianone Methyl Enol Ether via ACC Alkylation and Evaluation of their Anti-HIV Activity" Bioorg. Med. Chem. Lett. 2011, 21, 2406–2409.

  23. Yost, J. M.; Alfie, R.; Tarsis, E. T.; Coltart, D. M. "Direct Carbon–Carbon Bond Formation via Soft Enolization: Aldol Addition of α-Halogenated Thioesters" Chem. Commun. 2011, 47, 571–572.

    • Invited submission to Emerging Investigators Issue.
  24. Krenske, E. H.; Houk, K. N.; Lim,D.; Wengryniuk, S. E.; Coltart, D. M. "The Origins of Stereoselectivity in the α-Alkylation of Chiral Hydrazones" J. Org. Chem. 2010, 75, 8578–8584.
  25. Garnsey, M. R.; Lim, D.; Yost, J. M.; Coltart, D. M. "Development of a Strategy for the Asymmetric Synthesis of Polycyclic Polyprenylated Acylphloroglucinols via N-Amino Cyclic Carbamate Hydrazones: Application to the Total Synthesis of (+)-Clusianone" Org. Lett. 2010, 12, 5234-5237.

  26. Sauer, S. J.; Garnsey, M. R.; Coltart, D. M. "Direct Carbon–Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled Syn-Aldol Addition of α-Halo Thioesters" J. Am. Chem. Soc. 2010, 132, 13997–13999.

    • Featured in Synfacts, 2010, 1388.

  27. Kohler, M. C; Yost, J. M.; Garnsey, M. R.; Coltart, D. M. "Direct Carbon–Carbon Bond Formation via Soft Enolization: A Biomimetic Asymmetric Mannich Reaction of Phenylacetate Thioesters" Org. Lett. 2010, 12, 3376–3379.

  28. Hatcher, J. M.; Coltart, D. M. "Copper-(I) Catalyzed Addition of Grignard Reagents to In Situ-Derived N-Sulfonyl Azoalkenes: An Alkylation Procedure Applicable to the Formation of up to Three Contiguous Quaternary Centers" J. Am. Chem. Soc. 2010, 132, 4546–4547.

    • Featured in Synfacts, 2010, 813.
    • Highlighted in: New Methods for Carbon–Carbon Bond Construction, Organic Chemistry Portal, February 2011.
  29. Zhou, G.; Lim, D.; Fang, F.; Coltart, D. M. "A Practical Synthesis of β-Keto Thioesters via Direct Crossed-Claisen Coupling of Thioesters and N-Acylbenzotriazoles" Synthesis 2009, 3350–3352.

  30. Yost, J. M.; Garnsey, M. R.; Kohler, M. C.; Coltart, D. M. "Direct Carbon–Carbon Bond Formation via Soft Enolization of Thioesters: An Operationally Simple Mannich Addition Reaction" Synthesis 2009, 56–58.

    • Invited submission to 40th anniversary issue.
  31. Tarsis, E. T.; Gromova, A.; Lim, D.; Zhou, G.; Coltart, D. M. "Overcoming the Limitations of the Baylis-Hillman Reaction: A Rapid and General Synthesis of α-Alkenyl β-Hydroxy Thioesters" Org. Lett. 2008, 10, 4819–4822

  32. Zhou, G.; Lim, D.; Coltart, D. M. "Direct Carbon–Carbon Bond Formation via Chemoselective Soft Enolization of Thioesters: A Remarkably Simple and Versatile Crossed-Claisen Reaction Applied to the Synthesis of LY294002" Org. Lett. 2008, 10, 3809–3812.

    • Featured in Synfacts, 2008, 1314.
    • Highlighted as a name reaction in: Acetoacetic-Ester Condensation/Claisen Condensation, Organic Chemistry Portal, September 2008.

  33. Lim, D.; Coltart, D. M. "Simple and Efficient Asymmetric α-Alkylation and α,α-Bisalkylation of Acyclic Ketones Using Chiral N-Amino Cyclic Carbamate Hydrazones" Angew. Chem. Int. Ed. 2008, 47, 5207–5210.

    • Featured in: (a) Chemical and Engineering News, 2008, 86, 48–49. b) Chemistry World, June 13, 2008. (c) Drug Discovery and Development, July 1, 2008. (d) The Journal of Young Investigators, June 17, 2008.
  34. Lim, D.; Zhou, G.; Livanos, A. E.; Fang, F.; Coltart, D. M. "MgBr2×OEt2-Promoted Coupling of Ketones and Activated Acyl Donors via Soft Enolization: A Practical Synthesis of 1,3-Diketones" Synthesis, 2008, 2148–2152.

  35. Zhou, G.; Yost, J. M.; Sauer, S.; Coltart, D. M. "A Facile and Efficient Anti-Selective Four-Component Direct Aldol Addition via Chemoselective Thioester Enolate Formation" Org. Lett. 2007, 9, 4663–4665.

    • Featured in Synfacts, 2008, 56.

  36. Lim, D.; Fang, F.; Zhou, G.; Coltart, D. M. "Direct Carbon–Carbon Bond Formation via Soft Enolization: A Facile and Efficient Synthesis of 1,3-Diketones" Org. Lett. 2007, 9, 4139–4142.

    • Highlighted in: New Methods for Carbon–Carbon Bond Construction, Organic Chemistry Portal, June 2008.

  37. Zhou, G.; Yost, J. M.; Coltart, D. M. "A Direct Aldol Addition of Simple Thioesters Employing Soft Enolization" Synthesis 2007, 478–482.

    • Invited Paper

  38. Yost, J. M.; Zhou, G.; Coltart, D. M. "A Facile and Efficient Direct Aldol Addition of Simple Thioesters" Org. Lett. 2006, 8, 1503–1506.

    • Featured in Synfacts, 2006, 591.
    • Chosen as a: Best Synthetic Method: Carbon–Carbon Bond Formation, Organic Chemistry Portal, May 2007.


    Graduate Postdoctoral

  39. Clive, D. L. J.; Hisaindee, S.; Coltart, D. M. "Derivatized Amino Acids Relevant to Protein Synthesis by Native Chemical Ligation" J. Org. Chem. 2003, 68, 9247–9254.
  40. Coltart, D. M.; Danishefsky, S. J. "A Novel Synthetic Approach to the 8,10-Dimethyl Anti-Syn-Anti Perhydrophenanthrene Skeleton" Org. Lett. 2003, 5, 1289–1292.
  41. Keding, S. J.; Endo, A.; Biswas, K.; Zatorski, A.; Coltart, D. M.; Danishefsky, S. J. "Hydroxynorleucine as a Glycosyl Acceptor is an Efficient Means for Introducing Amino Acid Functionality in to Complex Carbohydrates" Tetrahedron Lett. 2003, 44, 3413–3416.
  42. Ragupathi, G.; Coltart, D. M.; Williams, L. J.; Koide, F.; Kagan, E.; Allen, J.;Harris, C.; Glunz, P. W.; Livingston, P. O.;* Danishefsky, S. J.* "On the Power of Chemical Synthesis: Immunological Evaluation of Models for Multiantigenic Carbohydrate-Based Cancer Vaccines" Proc. Natl. Acad. Sci. (U.S.A.) 2002, 99, 13699–13704.
  43. Biswas, K.; Coltart, D. M.; Danishefsky, S. J. "Construction of Carbohydrate-Based Antitumor Vaccines: Synthesis of Glycosyl Amino Acids by Olefin Cross-Metathesis" Tetrahedron Lett. 2002, 43, 6107–6110.
  44. Coltart, D. M.; A. K. Royyuru; Williams, W. J.; Glunz, P. W.; Sames, D.; Kuduk, S. D.; Schwarz, J. B.; Chen, X.-T.; Danishefsky, S. J.; Live, D. H. "Principles of Mucin Architecture: Structural Studies on Synthetic Glycopeptides Bearing Clustered Mono-, Di-, Tri- and Hexasaccharide Glycodomains" J. Am. Chem. Soc. 2002, 124, 9833–9844.
  45. Ragupathi, G.; Deshpande, P. P.; Coltart, D. M.; Kim, H. J.; Williams, L. J.; Danishefsky, S. J.; Livingston, P. O.* "Constructing an Adenocarcinoma Vaccine: Immunization of Mice with Synthetic KH-1 Nonasaccharide Stimulates Anti-KH-1 and Anti-Ley Antibodies" Intl. J. Cancer 2002, 99, 207–212.
  46. Clive, D. L. J.; Coltart, D. M.; Zhou, Y.; de Lima, D. P.; Yang, H.; Lewanczuk, R. Z. "Synthesis of the Naturally Occurring ACE Inhibitors (–)-A58365A and (–)-A58365B, and of an Unnatural but Biologically Active Analog" In Actualité de Chimie Thérapeutique, French Society of Medicinal Chemistry, 2002, 28th series, 21–50.
  47. Coltart, D. M. "Peptide Segment Coupling by Prior Ligation and Proximity-Induced Intramolecular Acyl Transfer" Tetrahedron 2000, 56, 3449–3491. (Review)
  48. Pelisson, M. M.; da Silva, G. V. J.; Clive, D. L. J.; Coltart, D. M.; Hof, F. A. "Studies on the Preparation of 3,4-Disubstituted 2-Methoxypyridines" J. Heterocyclic Chem. 1999, 36, 653–658.
  49. Clive, D. L. J.; Coltart, D. M.; Zhou, Y. "Synthesis of the Angiotensin-Converting Enzyme Inhibitors (–)-A58365A and (–)-A58365B from a Common Intermediate" J. Org. Chem. 1999, 64, 1447–1454.
  50. Clive, D. L. J.; Coltart, D. M. "Synthesis of the Angiotensin-Converting Enzyme Inhibitor (±)-A58365A" Tetrahedron Lett. 1998, 39, 2519–2522.
  51. Coltart, D. M.; Charlton, J. L. "The Asymmetric Synthesis of Aryltetralin Lignans: (–)-Isolariciresinol Dimethyl Ether and (–)-Deoxysikkimotoxin" Can. J. Chem. 1996, 74, 88–94.

    Book Chapters and Encyclopedia Articles

  52. Kohler, M. C.; Wengryniuk, S. E.; Coltart, D. M. "Asymmetric Alkylations in Stereoselective Synthesis". In Stereoselective Synthesis of Drugs and Natural Products; Andrushko, V.; Andrushko, N. Eds. Wiley-Blackwell: 2013, pp. 183–213. (Book chapter)
  53. Hatcher, J. M.; Coltart, D. M. "Bis(phenylthio)methane". In Encyclopedia of Reagents for Organic Synthesis; Fuchs, P. L. Ed.; John Wiley & Sons: 2011. (Encyclopedia Article)
  54. Yost, J. M.; Knight, J. D.; Coltart, D. M. "Tris(2-carboxyethyl)phosphine Hydrochloride". In Encyclopedia of Reagents for Organic Synthesis; Crich, D. Ed.; John Wiley & Sons: 2009. (Encyclopedia Article)

  55. Garnsey, M. R.; Wengryniuk, S. E.; Coltart, D. M. "Triphenylmethanethiol". In Encyclopedia of Reagents for Organic Synthesis; Crich, D. Ed.; John Wiley & Sons: 2009. (Encyclopedia Article)