Publications
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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.
- 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).
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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.
- Rastelli, E. J.; Coltart, D. M. " Synthesis and Biological Activity of Apratoxin Derivatives " Tetrahedron 2017, 74, 2269–2290.
- 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.
- 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.
- 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.
- 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.
- Rastelli, E. J.; Coltart, D. M. "Asymmetric Synthesis of (+)-anti- and (–)-syn-Mefloquine Hydrochloride" J. Org. Chem. 2016, 81, 9567–9575.
- 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.
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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.
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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".
- 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.
- 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.
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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.
- 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.
- 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.
- Robertson, B. D.; Wengryniuk, S. E.; Coltart, D. M. "Asymmetric Total Synthesis of Apratoxin D" Org. Lett. 2012, 14, 5192–5195.
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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. -
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. -
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.
- 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.
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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.
- 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.
- 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.
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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.
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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.
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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.
- 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.
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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.
- 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
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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.
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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.
- 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.
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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.
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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.
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Zhou, G.; Yost, J. M.; Coltart, D. M. "A Direct Aldol Addition of Simple Thioesters Employing Soft Enolization" Synthesis 2007, 478–482.
- Invited Paper
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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
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- Coltart, D. M. "Peptide Segment Coupling by Prior Ligation and Proximity-Induced Intramolecular Acyl Transfer" Tetrahedron 2000, 56, 3449–3491. (Review)
- 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.
- 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.
- Clive, D. L. J.; Coltart, D. M. "Synthesis of the Angiotensin-Converting Enzyme Inhibitor (±)-A58365A" Tetrahedron Lett. 1998, 39, 2519–2522.
- 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
- 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)
- 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)
- 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)
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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)