Zakarian Group

Li, Y.; Paola, E.; Wang, Z.; Menard, G,; Zakarian, A. Lithium Enolate with  a Lithium-Alkyne Interaction in the Enantioselective Construction of Quaternary Carbon Centers: Concise Synthesis of (+)-Goniomitine. Angew. Chem. Int. Ed. 2022, e202209987.

Podunavac, M.; Mailyan, A. K.; Jackson, J. J.; Lovy, A.; Farias, P.; Huerta, H.; Molgó, J.; Cardenas, C.; Zakarian, A. Scalable Total Synthesis, IP3R Inhibitory Activity of Desmethylxestospongin B, and Effect on Mitochondrial Function and Cancer Cell Survival. Angew. Chem. Int. Ed. 2021, 60, 11278-11282.

Lacharity, J. J.; Mailyan, A. K.; Chen, K. Y.;  Zakarian, A. Concise Synthesis of (+)-[¹³C₄]-Anatoxin-a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion. Angew.  Chem. Int. Ed.  2020, 59, 11364-11368..

Gladfelder, J. J.; Ghosh, S.; Podunavac, M.; Cook, A. W.; Ma, Y.; Woltornist, R. A.; Keresztes, I.; Hayton, T., W.; Collum, D. B.; Zakarian, A. Enantioselective Alkylation of 2-Alkylpyridines Controlled by Organolithium Aggregation. J. Am. Chem. Soc. 2019, 141, 15024-15028.

Lacharity, J. J.; Zakarian A. Evolution of a Chemical Strategy Toward the Synthesis of Unsymmetrically Oxidized Nuphar Alkaloids. Synlett 2019, 30, 1632-1642.

Yu, K.; Miao, B.; Wang, W.; Zakarian A. Direct Enantioselective and Regioselective Alkylation of β,γ-Unsaturated Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries. Org. Lett. 2019, 21, 1930-1934.

Fournier, J.; Chen, K.; Mailyan, A. K.; Jackson, J. J.; Buckman, B. O.; Emayan, K.; Yuan, S.; Rajagopalan, R.; Misialek, S.; Adler, M.; Blaesse, M.; Griessner, A.; Zakarian, A. Total Synthesis of Covalent Cysteine Protease Inhibitor N‐Desmethyl Thalassospiramide C and Crystallographic Evidence for Its Mode of Action. Org. Lett. 2019, 21, 508-512.

Podunavac, M.; Lacharity, J. J.; Jones, K. E.; Zakarian, A. Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkyloxy Esters. Org. Lett. 2018, 20, 4867-4870.

Reid, B. T.; Mailyan, A. K.; Zakarian, A. Total Synthesis of (+)-Guadinomic Acid via Hydroxyl-Directed Guanidylation. J. Org. Chem. 2018, 83, 9492-9496.

Mailyan, A. K.; Chen, J. L.; Li, W.; Keller, A. A.; Sternisha, S. M.; Miller, B. G.; Zakarian, A. Short Total Synthesis of [¹⁵N₅]-Cylindrospermopsins from ¹⁵NH₄Cl Enables Precise Quantification of Freshwater Cyanobacterial Contamination. J. Am. Chem. Soc. 2018, 140, 6027-6032.

Lacharity, J. J.; Fournier, J.; Lu, P.; Mailyan, A. K.; Herrmann, A. T.; Zakarian, A. Total Synthesis of Unsymmetrically Oxidized Nuphar Thioalkaloids via Copper-Catalyzed Thiolane Assembly.  J. Am. Chem. Soc. 2017, 139, 13272-13275. 

Cano, R.; Zakarian, A.; McGlacken, G. P. Direct Asymmetric Alkylation of Ketones: Still Unconquered. Angew. Chem. Int. Ed., 2017, 56, 9278-9290.

Burns, A. S.; Wagner, A. J.; Fulton, J. L.; Young, K.; Zakarian, A.; Rychnovsky, S. D. Determination of the Absolute Configuration of β-Chiral Primary ALcohols Using the Competing Enantioselective Conversion Method. Org. Lett., 2017, 19, 2953-2956.

Martinez, J. A.; Xiao, Q.; Zakarian, A.; Miller, B. G. Antidiabetic Disruptors of the Glucokinase-Glucokinase Regulatory Protein Complex Reorganize a Coulombic Interface. Biochemistry, 2017, 56, 3150-3157.

Yu, K.; Lu, P.; Jackson, J. J.; Nguyen, T. D.; Alvarado, J.; Stivala, C. E.; Ma. Y.; Mack, K. A.; Hayton, T. W.; Collum, D. B.; Zakarian, A. Lithium Enolates in the Enantioselective Construction of Tetrasubstituted Carbon Centers wtih Chiral Lithium Amides as Noncovalent Stereodirecting Auxiliaries. J. Am. Chem. Soc., 2017, 139, 527-533.

Mailyan, A. K.;  Young, K.; Chen, J. L.; Reid, B. T.; Zakarian, A. Stereoselective Synthesis of Cyclic Guanidines by Directed Diamination of Unactivated Alkenes. Org. Lett., 2016, 18, 5532-5535.

Alvarado, J.; Fournier, J,; Zakarian, A. Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C-O Bond Formation under Mild Conditions. Angew. Chem. Int. Ed., 2016, 55, 11625-11628.

Ma, Y.; Mack, K. A.; Liang, J.; Keresztes, I.; Collum, D. B.; Zakarian, A. Mixed Aggregates of the Dilithiated Koga Tetraamine: NMR Spectroscopic and Computational Studies. Angew. Chem. Int. Ed., 2016, 55, 10093-10097.

Mailyan, A. K.; Eickhoff, J. A.; Minakova, A. S.; Gu, Z.; Lu, P.; Zakarian, A. Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis. Chem. Rev., 2016, 116, 4441-4557.

Kobayashi, H.; Eickhoff, J. A.; Zakarian, A. Synthesis of 2-Aminoazoles from Thioesters via ⍺-Heterosubstituted Ketones by Copper-Mediated Cross-Coupling. J. Org. Chem., 2015, 80, 9989-9999. 

Jackson, J. J.; Kobayashi, H.; Steffens, S. D.; Zakarian, A. 10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-Dragmacidin D. Angew. Chem. Int. Ed., 2015, 54, 9971-9975. 

Xiao, Q.; Young, K.; Zakarian, A. Total Synthesis and Structural Revision of (+)-Muironolide A.  J. Am. Chem. Soc., 2015, 137, 5907-5910.

Young, K.; Xiao, Q.; Zakarian, A. Toward the Synthesis of Muironolide A: Synthesis and Structure of Heteroleptic Lanthanide-Terpyridine Complexes with 2-Oxo Amides. Eur. J. Org. Chem., 2015, 11, 2337-2341.

Stivala, C. E.; Benoit, E.; Aráoz, R.; Servent, D.; Novikov, A.; Molgó, J.; Zakarian, A. Synthesis and Biology of Cyclic Imine Toxins, an Emerging Class of Potent, Globally Distributed Marine Toxins. Nat. Prod. Rep., 2015, 32, 411-435. 

Lu, P.; Jackson, J. J.; Eickhoff, J. A.; Zakarian, A. Direct Enantioselective Conjugate Addition of Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries. J. Am. Chem. Soc. 2015, 137, 656-659.

Lu, P.; Mailyan, A.; Gu, Z.; Guptill, D. M.; Wang, H.; Davies, H. M. L.; Zakarian, A. Enantioselective Synthesis of (-)-Maoecrystal V by Enantiodetermining C-H Functionalization. J. Am. Chem. Soc., 2014, 136, 17738-17749.

Alvarado, J.; Herrmann, A. T.; Zakarian, A. Stereoselective a-Fluorination of N-Acyloxazolidinones at Room Temperature within 1 h. J. Org. Chem., 2014, 79, 6206-6220.

Mabe, P. J.; Zakarian, A. Asymmetric Radical Addition of TEMPO to Titanium Enolates. Org. Lett., 2014, 16, 516-519.

Lu, P.; Gu, Z.; Zakarian, A. Total Synthesis of Maoecrystal V: Early-Stage C-H Functionalization and Lactone Assembly by Radical Cyclization. J. Am. Chem. Soc., 2013, 135, 14552-14555.

Xiao, Q.; Young, K.; Zakarian, A. An Efficient Synthesis of the Fully Elaborated Isoindolinone Unit of Muironolide A. Org. Lett., 2013, 15, 3314-3317.

Ma, Y.; Stivala, C. E.; Wright, A. M.; Hayton, T.; Liang, J.; Keresztes, I.; Lobkovsky, E.; Collum, D. B.; Zakarian, A. Enediolate-Dilithium Amide Mixed Aggregates in the Enantioselective Alkylation of Arylacetic Acids: Structural Studies and a Stereochemical Model. J. Am. Chem. Soc. 2013, 135, 16853-16864.

Xiao, Q.; Jackson, J. J.; Basak, A.; Bowler, J. M.; Miller, B. G.; Zakarian, A. Enantioselective Synthesis of Tatanans A-C and Reinvestigation of their Glucokinase-Activating Properties. Nature Chemistry. 2013, 5, 410-416.

Hess, P.; Abadie, E.; Hervé, Berteaux, T.; Séchet, V.; Aráoz, R.; Molgó, J.; Zakarian, A.; Manoëlla, S.; Rundberget, T.; Miles, C. O.; Amzil, Z. Pinnatoxin G is Responsible for Atypical Toxicity in Mussels (Mytilus galloprovincialis)  and Clams (Vernerupis decussata) from Ingril, a French Mediterranean Lagoon. Toxicon. 2013, 75, 16-26.

Jackson, J. J.; Stivala, C. E.; Iorga, B. I.; Molgo, J.; Zakarian, A. Stability of Cyclic Imine Toxins: Interconversion of Pinnatoxin Amino Ketone and Pinnatoxin A in Aqueous Media. J. Org. Chem. 2012, 77, 10435-10440.

Stivala, C. E.; Gu, Z.; Smith, L. L.; Zakarian, A. Studies Toward the Synthesis of Spirolide C: Exploration into the Formation of the 23-Membered All-Carbon Macrocyclic Framework. Org. Lett. 2012, 14, 804-807.

Aráoz, R.; Ramos, S.; Pelissier, F.; Guérineau, V.; Benoit, E.; Vilariño, N..; Botana, L. M.; Zakarian, A.; Molgó, J. Coupling the Torpedo Microplate-Receptor Binding Assay with Mass Spectrometry to Detect Cyclic Imine Neurotoxins. Anal. Chem. 2012, 84, 10445-10453.

Herrmann, A. T.; Smith, L. L.; Zakarian, A. A Simple Method for Asymmetric Trifluoromethylation of N-acyl Oxazolidinones vis Ru-Catalyzed Radical Addition to Zirconium Enolates. J. Am. Chem. Soc. 2012, 134, 6976-6979.

Gu, Z.; Zakarian, A. Studies Toward the Synthesis of Maoecrystal-V. Org. Lett. 2011, 13, 1080-1082.

Herrmann, A. T.; Martinez, S. R.; Zakarian, A. A Concise Asymmetric Total Synthesis of (+)-Brevisamide. Org. Lett. 2011, 13, 3636-3639.

Araoz, R.; Molgoi, J.; Benoit, E.; Iorga, B. I.; Servent, D.; Fruchart-Gaillard, C.; Gu, Z.; Stivala, C.; Zakarian, A. Total Synthesis of Pinnatoxins A and G and Revision of the Mode of Action of Pinnatoxin A. J. Am. Chem. Soc. 2011, 133, 10499-10511.

Gu, Z.; Herrmann, A. T.; Zakarian, A. Dual Ti-Ru Catalysis in the Direct Radical Haloalkylation of N-acyl Oxazolidinones. Angew. Chem. Int. Ed. 2011, 50, 7136-7139.

Stivala, C. E.; Zakarian, A. Highly Enantioselective Direct Alkylation of Arylacetic Acids with Chiral Lithium Amides as Traceless Auxiliaries. J. Am. Chem. Soc. 2011, 133, 11936-11939.

Ilardi, E. A.; Zakarian, A. Effecient Total Synthesis of Dysidenin, Dysidin, and Barbamide. Chemistry - An Asian Journal, 2011, 6, 2260-2263.

Beaumont, S.; Ilardi, E. A.; Monroe, L. R.; Zakarian, A. Valence Tautomerism in Titanium Enolates: Catalytic Radical Haloalkylation and Application in the Total Synthesis of Neodysidenin. J. Am. Chem. Soc. 2010, 132, 1482-1483.

Herrmann, A. T.; Saito, T.; Stivala, C. E.; Tom, J.; Zakarian, A. Regio- and Stereocontrol in Rhenium-Catalyzed Transposition of Allylic Alcohols. J. Am. Chem. Soc. 2010, 132, 5962-5963.

Gu, Z.; Herrmann, A. T.; Stivala, C. E.; Zakarian, A. Stereoselective Construction of Adjacent Quaternary Chiral Centers by the Ireland-Claisen Rearrangement: Stereoselection with Esters of Cyclic Alcohols. Synlett, 2010, 11, 1717-1722.

Gu, Z.; Zakarian, A. Total Synthesis of Rhazinilam: Axial to Point Chirality Transfer in an Enantiospecific Pd-Catalyzed Transannular Cyclization. Org. Lett. 2010, 12, 4224-4227.

Beaumont, S.; Ilardi, E. A.; Tappin, N. D. C.; Zakarian, A. Marine Toxins with Spiroimine Rings: Total Synthesis of Pinnatoxin A. Eur. J. Org. Chem. 2010, 30, 5743-5765.

Gu, Z.; Zakarian, A. Concise Total Synthesis of Sintokamides, A, B, and E by a Unified, Protecting-Group-Free Strategy. Angew. Chem. Int. Ed. 2010, 49, 9702-9705.

Stivala, C. E.; Zakarian, A. Studies Toward the Synthesis of Spirolides: Assembly of the Elaborated E-ring Fragment. Org. Lett. 2009, 11, 839-842.

Ilardi, E. A.; Isaacman, M. J.; Qin, Y.; Shelly, S. A.; Zakarian, A. Consecutive Sigmaropic Rearrangements in the Enantioselective Total Synthesis of (-)-Joubertinamine and (-)-Mesembrine. Tetrahedron, 2009, 65, 3261-3269.

Stivala, C. E.; Zakarian, A. Total synthesis of (+)-Pinnatoxin A. J. Am. Chem. Soc. 2008, 130, 3774-3776.

Zakarian, A.; Lu, C. Total Synthesis of (+/-)-Trichodermamide B and of a Putative Biosynthetic Precursor to Aspergillazine A using an Oxaza-Cope Rearrangement. Angew. Chem. Int. Ed. 2008, 47, 6829-6831.

Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Hexafluoroisopropanol as a Unique Solvent for Stereoselective Iododesilylation of Vinylsilanes. Org. Lett. 2008, 10, 1727-1730.

Lu, C.; Zakarian, A. Studies Toward the Synthesis of Pinnatoxins: The B, C, D-Dispiroketal Fragment. Org. Lett. 2007, 9, 3161-3163.

Stivala, C. E.; Zakarian, A. Studies Toward the Synthesis of Pinnatoxins: The Spiroimine Fragment. Tetrahedron Lett. 2007, 48, 6845-6848.

Qin, Y.; Stivala, C. E.; Zakarian, A. Acyclic Stereocontrol in the Ireland-Claisen Rearrangement of Alpha-Branched Esters. Angew. Chem. Int. Ed. 2007, 46, 7466-7469.

Zakarian, A., Lu, C. Development of the 1,2-Oxaza-Cope Rearrangement. J. Am. Chem. Soc. 2006, 128, 5356-5357.

Pelc, M. J.; Zakarian, A. Synthesis of the A, G-Spiroimine of Pinnatoxins by a Microwave-Assisted Tandem Claisen-Mislow-Evans Rearrangement. Tetrahedron Lett. 2006, 47, 7519-7523.

Pelc, M. J.; Zakarian, A. An Approach to the Imine Ring System of Pinnatoxins. Org. Lett. 2005, 7, 1629-1631.

Zakarian, A.; Batch, A.; Holton, R. A. A Convergent Total Synthesis of Hemibrevetoxin B. J. Am. Chem. Soc. 2003, 125, 7822-7824.