Gagik G. Melikyan
Chemistry and Biochemistry

EDUCATION
Ph.D., Institute of Elementorganic Compounds, Moscow
D.Sc. (Doctor of Sciences), Institute of Organic Chemistry, Yerevan, Armenia
POSTDOCTORAL APPOINTMENTS
Alexander von Humboldt Fellow, University of Erlangen-Nürnberg, Germany, 1990-1992
Adjunct Professor of Chemistry, University of Oklahoma, 1993-1995
COURSES TAUGHT
Chemistry 235, Introductory Organic Chemistry
Chemistry 331, Organic Chemistry I
Chemistry 331L, Organic Chemistry I Laboratory
Chemistry 332, Organic Chemistry II
Chemistry 332L, Organic Chemistry II Laboratory
Chemistry 333, Principles of Organic Chemistry I
Chemistry 333L, Principles of Organic Chemistry I Laboratory
Chemistry 334, Principles of Organic Chemistry II
Chemistry 595F, Organometallic Chemistry
RESEARCH INTERESTS
Organic / Organometallic / Medicinal Chemistry
Asymmetric synthesis; radical and ionic reactions of transition metal-complexed unsaturated systems; synthetic methods based on new physical principles; therapeutic agents for breast cancer treatment; aromatase inhibitors; unnatural female hormones; nonsteroidal hormones; antioxidants; supplements; cosmetics; consumer product adulteration; environmental laws; public health-related legislation; history of chemistry; data analysis.
AWARDS
2002 Polished Apple Award, University Ambassadors, CSUN
2008 Outstanding Faculty Award, CSUN
2008 Foreign Member, National Academy of Sciences, Yerevan, Armenia
2010 Jerome Richfield Scholar Award, CSUN
2015 Kennedy Center Stephen Sondheim Inspirational Teacher Award, Washington, D.C.
2019 Fellow, American Association for the Advancement of Science (AAAS), Washington, D.C.
REPRESENTATIVE PUBLICATIONS (from a total of 90)
- “Cobalt-Complexed Acetylenic Tetrads, a Molecular Scaffold for Quadruple Ionic Functionalization Reactions” Melikyan, G. G.; Babayans, N.; Kalpakyan, N.; Herrera, C.; Rublev, P.; Tkachenko, N. V.; Boldyrev, A. I. Organometallics (2024) 43, 1964-1987.
- “Cobalt-Mediated Radical Cyclizations: Stereoselective Synthesis of Cyclopentanes, Cyclohexanes, and Tetralins” Melikyan, G. G.; Artashyan, E.; Guarina, Sh.; Babayans, N.; Parunyan, M.; Daravidian, V.; Mishra, A. Organometallics (2023) 42, 547−564.
- Book chapter: Melikyan, G. G.; Artashyan, E. Ionic and Radical Reactions of pi-Bonded Cobalt Complexes. In: Cobalt Catalysis in Organic Synthesis: Methods and Reactions. Eds. Hapke, M.; Hilt. G; Wiley-VCH Verlag GmbH & Co, 2020, 1st Ed., Ch. 6, pp. 207-234.
- "Acquiring a Prognostic Power in Co2(CO)6-Mediated, Cobaltocene-Induced Radical Dimerizations of Propargyl Triflates" Melikyan, G. G.; Davis, R.; Anker, B.; Meron, D.; Duncan, K. Organometallics (2016) 35, 4060-4070.
- "Acquiring and Exploiting Persistency of Propargyl Radicals: Novel Paradigms" Melikyan, G. G.; Davis, R.; Cappuccino, S. Organometallics (2016) 35, 2854-2867.
- "Radical Reactions of 1,4-Alkadiynes: Metal Coordination as an Effective Tool for Controlling the Regio- and Stereoselectivity of the C-C Bond Formation" Melikyan, G. G.; Anker, B. Organometallics (2015) 34, 4194-4197.
- Review: "Propargyl Radical Chemistry: Renaissance Instigated by Metal Coordination" Melikyan, G. G. Accounts of Chemical Research (2015) 48, 1065-1079.
- "Assembling Contiguous Quaternary Carbons Atoms: Regio- and Stereoselective Rearrangements in Cobalt-Directed Radical Reactions of 1,4-Enynes" Melikyan, G. G.; Hughes, R.; Rivas, B.; Duncan, K.; Sahakyan, N. Organometallics (2015) 34, 242-253.
- "Radical Reactions of the Cobalt-Complexed Propargyl Acetals: Inter- and Intramolecular Variants" Melikyan, G. G.; Voorhees, E.; Sepanian, R. Organometallics (2014) 33, 69-83.
- "Impact of Reducing Agent, Temperature, and Substrate Topology on Diastereoselectivity of the Intermolecular Coupling Reactions, or How “Free” Are Cobalt-Complexed Propargyl Radicals?" Melikyan, G. G.; Carlson, L.; Sahakyan, N.; Floruti, A.; Garrison, M. Dalton Transactions (2013) 42, 14801–14812.
- "Cobaltocene-Induced Low-Temperature Radical Coupling Reactions in a Cobalt-Alkyne Series" Melikyan, G. G.; Rivas, B.; Harutyunyan, S.; Carlson, L.; Sepanian, R. Organometallics (2012) 31, 1653-1663.
- "1,3-Steric Induction in Intermolecular Radical Reactions Mediated by a Co2(CO)6-Metal Core" Melikyan, G. G.; Spencer, R.; Rowe, A. Organometallics (2010) 29, 3556-3562.
- "Inter- and Intramolecular Isocarbon Couplings of Cobalt-Complexed Propargyl Radicals: Challenging the Consensus" Melikyan, G. G.; Spencer, R. Tetrahedron (2010) 66, 5321-5328.
- "Carbon Tether Rigidity as a Stereochemical Tool Directing Intramolecular Radical Cyclizations" Melikyan, G. G.; Vorhees, E.; Wild, C.; Spencer, R.; Molnar, J. Tetrahedron Letters (2010) 51, 2287-2290.
- "Stereoselective Synthesis of meso-1,5-Cyclodecadiynes" Melikyan, G. G.; Spencer, R.; Abedi, E. J. Org. Chem. (2009) 74, 8541-8546.
- "Cobalt-Complexed Propargyl Cations: Generation under Neutral Conditions and Spontaneous, High-Temperature Conversion to Propargyl Radicals" Melikyan, G. G.; Sepanian, R.; Spencer, R.; Rowe, A.; Toure, P. Organometallics (2009) 28, 5541-5549.
- "High-Temperature Reaction of a Co2(CO)6-Complexed Propargyl Cation" Melikyan, G. G.; Mikailian, B.; Sepanian, R.; Toure, P. J. Organomet. Chem. (2009) 694, 785-794.
- "Intramolecular Radical Cyclizations of Co2(CO)6-Complexed Propargyl Radicals: Synthesis of d,l- and meso-1,5-Cyclodecadiynes" Melikyan, G. G.; Wild, C.; Toure, P. Organometallics (2008) 27, 1569-1581.
- "Cross-Coupling of Cobalt-Complexed Propargyl Radicals: Metal Core- and alpha- and gamma-Aryl-Induced Chemo- and Diastereoselectivity" Melikyan, G. G.; Floruti, A.; Devletyan, L.; Toure, P.; Dean, N.; Carlson, L. Organometallics (2007) 26, 3173-3182.
- "Tetrahydrofuran-Mediated Stereoselective Radical C-C Bond Formation in Dicobalthexacarbonyl-Propargyl Complexes" Melikyan, G. G.; Villena, F.; Floruti, A.; Sepanian, S.; Sarkissian, H.; Rowe, A.; Toure, P.; Mehta, D.; Christian, N.; Myer, S.; Miller, D.; Scanlon, S.; Porazik, M.; Gruselle, M. Organometallics (2006) 25, 4680-4690.
- Book chapter: Gagik Melikyan “Ligand-Based Organometallic Radical Chemistry: An Emerging Interdisciplinary Field” in: Frontiers in Organometallic Chemistry. Ed. M. A. Cato, Nova Science Publishers, 2006, Ch. 7, 155-190.
- "Spontaneous Generation and Stereoselective Coupling of Co2(CO)6-Complexed Propargyl Radicals" Melikyan, G. G.; Villena, F.; Sepanian, S.; Pulido, M.; Sarkissian, H.; Floruti, A. Organic Letters (2003) 5, 3395-3397.
- "Tetrahydrofuran - Mediated Radical Processes: Stereoselective Synthesis of dl-Hexestrol" Melikyan, G. G.; Sepanian, S.; Riahi, B.; Villena, F.; Jerome, J.; Ahrens, B.; McClain, R.; Matchett, J.; Scanlon, S.; Abrenica, E.; Paulsen, K.; Hardcastle, K. I. J. Organomet. Chem. (2003) 683, 324-330.
- "Thymidine 3',5'-Diphosphoric Acid Derived Cations and Radicals: Ab Initio Study" Toure, P.; Villena, F.; Melikyan, G. G. Organic Letters (2002) 4, 3989-3992.
- "Interaction of Propargyl Cation with Tetrahydrofuran: Thermodynamics, Kinetics, and Biological Relevance" Toure, P.; Myer, S.; Melikyan, G. G. J. Phys. Chem. A (2001) 105, 4579-4584.
- "Hydroalumination-Brominolysis of Vinylacetylenic Alcohols: A Novel Entry to E - and Z - Bromodienols, and Bromoallenols" Gharibian, H.; Palikyan, G.; Badanyan, Sh.H.; Paulsen, K.; Melikyan, G. G. Helv. Chim. Acta. (2000) 83, 3291-3294.
- "Manganese(II)/(III) Glycolates: Preparation, X-Ray Crystallographic Study, and Application in Radical Cycloaddition Reactions" Melikyan, G. G.; Amiryan, F.; Visi, M.; Hardcastle, K. I.; Bales, B. L. Inorg. Chim. Acta (2000) 308, 45-50.
- "Reduction of Metal-Stabilized alpha-CF3-Carbenium Ion Complexes under Mild Conditions: Synthesis, Structures, and Reactivity" Gruselle, M.; Malezieux, B.; Andres, R.; Amouri, H.; Vaissermann, J.; Melikyan, G. G. Eur. J. Org. Chem. (2000), 359-368.
- "Cobalt-Templated Radical Processes:Inter- and Intramolecular Coupling of Propargyl Radicals" Melikyan, G. G.; Deravakian, A.; Myer, S.; Yadegar, S.; Hardcastle, K. I.; Ciurash, J.; Toure, P. J. Organomet. Chem. (1999) 578, 68-75.
- Review: "Manganese-Based Organic and Bioinorganic Transformations" Melikyan, G. G. Aldrichimica Acta (1998), 50-64.
- "Overcoming a Longstanding Challenge: X-Ray Structure of a Co2(CO)6-Complexed Propargyl Cation" Melikyan, G. G.; Bright, S.; Monroe, T.; Hardcastle, K. I.; Ciurash, J. Angew. Chem. (1998) 110, 170-172; Angew. Chem. Int. Ed. (1998) 37, 161-164.
- "Tetrahydrofuran as a One-Electron Donor: Highly Diastereoselective Coupling of Cobalt-Complexed Propargyl Alcohol" Melikyan, G. G.; Deravakian, A. J. Organomet. Chem. (1997) 544, 143-145.
- Book chapter: "Radical Carbon-Carbon Bond-Forming Reactions Promoted by Trivalent Manganese" Melikyan, G. G. in Organic Reactions, Ed. Paquette, L., John Wiley, 1997, Vol. 49, Ch. 3, p. 427-675.
- "A Novel Synthetic Approach to Cycloocta-1,5-diynes and Cyclooct-3-ene-1,5-diynes" Melikyan, G. G.; Khan, M. A.; Nicholas, K. M. Organometallics (1995) 14, 2170-2172.
- Book chapter: "The Chemistry of Metal - Alkyne Complexes" Melikyan G. G.; Nicholas K. M. in Modern Acetylene Chemistry, Ed. Stang P.J., Diederich F., VCH Publishers, 1995, Ch. 4, 99-138.
- "Cobalt Cluster-Directed, Mn(III)-Mediated Chemo- and Stereoselective Radical Reaction of 1-Alken-3-ynes" Melikyan, G. G.; Vostrowsky, O.; Bauer, W.; Bestmann, H. J.; Khan, M.; Nicholas, K. M. J. Org. Chem. (1994) 59, 222-229.
- "A Novel and Efficient Synthesis of Cyclic and Acyclic 1,5-Alkadiynes by Selective Coupling of Co2(CO)6-Complexed Propargyl Radicals" Melikyan, G. G.; Combs, R. C.; Lamirand, J.; Khan, M.; Nicholas, K. M. Tetrahedron Lett. (1994) 363-366.
- Review: "Manganese(III)-Mediated Reaction of Unsaturated Systems" Melikyan, G. G. Synthesis (1993), 833-850.
- "µ-(3-4- -1-Alken-3-yne)Hexacarbonyldicobalt Complexes: Regioselective Radical Cyclocondensation, Mediated by Manganese(III) Acetate" Melikyan, G. G.; Vostrowsky, O.; Bauer, W.; Bestmann, H. J. J. Organometal. Chem. (1992) 423, C24-C27.
- "Dehydration of Co2(CO)6-Protected Tertiary Propargyl Alcohols. Stereo- and Regiochemistry. Synthesis of Enantiomerically Pure Manicone and Normanicone" Melikyan, G. G.; Mineif, A.; Vostrowsky, O.; Bestmann, H. J. Synthesis (1991) 8, 633-636.
- "Control of the Propargyl Radical Stabilization by the Carbon-Chain Length in Manganese(III)-Mediated Reactions of 1-Alken-3ynes. A Facile Synthetic Way to Long-Chain 4-Acetoxy-5-alkynoic Acids" Melikyan, G. G.; Mkrtchyan, V. M; Badanyan, Sh. O.; Vostrovsky, O.; Bestmann, H. J. Chem. Ber. (1991) 124, 2037-2040.
- "Synthesis of (S)-(+)-Manicone and (S)-(+)-Normanicone, Mandibular Gland Constituents of Myrmicine Ants" Martischonok, V.; Melikyan, G. G.; Mineif, A.; Vostrowsky, O.; Bestmann, H. J. Synthesis (1991), 560-564.
M. S. THESES
- Ionic Functionalization Reactions in Cobalt-Complexed Acetylenic Tetrads and Hexads (2023) Babayans, N.
- Enzymatic Transformations of Resveratrol from Red Wine (2017) Jensen, J. (jointly with Department of Family and Consumer Sciences)
- Allylic Rearrangements in Cobalt-Mediated Radical Coupling Reactions (2015) Gould, R.
- Transition Metal-Mediated Radical Reactions of Propargyl Acetals (2013) Voorhees, E.
- Radical Coupling Reactions Under Neutral Conditions and Their Biological Relevance (2010) Sepanian, R.
- Inter- and Intramolecular Radical C-C Bond Formation Mediated by a Transition Metal Core (2010) Spencer, R.
- Cobalt-Assisted Intramolecular Radical Cyclization Reactions (2008) Wild, C.
- Cross-Coupling of Cobalt-Complexed Propargyl Radicals: Chemo-, Regio-, and Diastereoselective Access to 3,4-Diaryl-1.5-hexadiynes (2008) Floruti, A.
- Topologically Diverse D,L-3,4-Diaryl-1,5-alkadiynes: Design, Stereoselective Synthesis and Biotesting (2006) Rowe, A.
- Novel Reactions of Ligand-Based Organometallic Radicals (2003) Villena, F.
- Novel Organometallic Probes for Biochemical Studies (2001) Riahi, B.
- Chiral Cobalt-Complexed Conjugated Enynes: Design, Synthesis and Radical Cycloaddition Reactions (1999) Yadegar, S.
- Coupling Reactions of Dicobalt Hexacarbonyl Propargyl Radicals (1999) Myer, S.