Armen Zakarian

Armen Zakarian
Professor

Contact Phone

(805) 893-3717

Office Location

Chem 2217

Specialization

Education

Dr. Zakarian received his Doctoral Degree in Chemistry in 2001 in the field of natural products synthesis, working in the group of Professor Robert Holton. He subsequently pursued his postdoctoral studies at the University of California, Irvine in the laboratories of Professor Larry Overman, between 2002 and 2004. After first four years in Florida, Dr. Zakarian joined the faculty at UC Santa Barbara in June 2008. He is a recipient of the Amgen Young Investigator Award, Eli Lilly Grantee Award, and the NSF Faculty Early Career Development Award.

Research

Research Group Website: http://www.chem.ucsb.edu/~zakarian/home.html

Research Objective

In our research, we are applying our core interest in the synthesis of complex natural products as a starting point to contributions in different fields of chemical science, including the development of organic synthesis on both strategic and methodological levels, asymmetric synthesis, development and applications of catalysis, and various aspects of bioorganic chemistry, especially the elucidation of the mode of action of unusual biologically active natural products.

As an example, in the past few years our efforts have focused on a subclass of marine toxins belonging to the cyclic imine group. We have achieved a scalable synthesis of one member in this class of complex natural products that enabled the elucidation of its mechanism of toxicity in collaboration with a research group in France. This research project also served as a starting point for our contributions to the development of new methodology based on enolate chemistry, which is an ongoing effort in our group.

Our research interests can be broadly defined as:

  • Development of synthetic methodology for asymmetric synthesis
  • Application of catalysis to problems in synthesis
  • Total Synthesis of Natural Products
  • Applications of chemistry to studying problems in biology

Publications

Selected Research Publications

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, JOC, 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, 3, p. 804-807

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, JACS, 2012, 134, 6976-6979

Gu, Z.; Zakarian, A., Studies toward the synthesis of maoecrystal-V, Org Lett, 2011, 13, 5, p. 1080-1082

Herrmann, A. T.; Martinez, S. R.; Zakarian, A., A concise asymmetric total synthesis of (+)-brevisamide, Org Lett, 2011, 13, 14, P. 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, JACS, 2011, 133, 27, p. 10499-10511

Gu, Z.; Herrmann, A. T.; Zakarian, A., Dual Ti-Ru catalysis in the direct radical haloalkylation of N-acyl oxazolidinones, Angewandte Chemie, 2011, 50, 31, p. 7136-7139

Stivala, C. E.; Zakarian, A., Highly enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries, JACS, 2011, 133, 31, p. 11936-11939

Ilardi, E. A.; Zakarian, A., Effecient total synthesis of dysidenin, dysidin, and barbamide, Chemistry - An Asian Journal, 2011, 6, p. 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, JACS, 2010,132, p. 1482-1483

Herrmann, A. T.; Saito, T.; Stivala, C. E.; Tom, J.; Zakarian, A., Regio- and stereocontrol in rhenium-catalyzed transposition of allylic alcohols, JACS, 2010, 132, p. 5962-5963

Gu, Z.; Herrmann, A. T.; Stivala, C. E.; Zakarian, A., Stereoselective construction of adjacent quaternary chiral centers by the Ireland-Claisent rearrangement: Stereoselection with esters of cyclic alcohols, Synlett, 2010, 11, p. 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, 19, p. 4224-4227

Beaumont, S.; Ilardi, E. A.; Tappin, N. D. C.; Zakarian, A., Marine toxins with spiroimine rings: total synthesis of pinnatoxin A, EJOC, 2010, 30, p. 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, doi: 10.1002/anie.201005354

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, 5743–5765.

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.

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

Lu, C.-D.; Zakarian, A. “Unified Total Synthesis of (±)-Trichodermamide B and the Putative Biosynthetic Precursor of (±)-Aspergillazine A Using the Oxaza-Cope Rearrangement” Angewandte Chemie, Int. Ed. 2008, 47,  6829–6831.

Stivala, C.; Zakarian, A. “Total Synthesis of (+)-Pinnatoxin A” J. Am. Chem. Soc. 2008, 130, 3774–3776.

  • Top 3 Most Read Article in JACS within three months after publication
  • Top 10 Most Read Article in JACS within a year after publication
  • Synthesis-of-the-months in Synfacts;
  • featured article in SynForms

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

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

Qin, Y.; Stivala, C. E., Zakarian, A. "Acyclic Stereocontrol in the Ireland-Claisen Rearrangement of alpha-Branched Esters" Angewandte Chemie, Int. Ed. 2007, 46, 7466-7469.

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