Contact info

Dept. Chemistry & Biochemistry

18111 Nordhoff Street
Northridge, California
91330-8262

Phone: (818) 677-3381
Fax: (818) 677-4068
E-mail: chemistry@csun.edu

Office: 2102 Eucalyptus Hall

Hours: Mon-Fri 8:00am-5:00pm

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Thomas G. Minehan

Thomas G. Minehan

ASSOCIATE PROFESSOR

Department of Chemistry and Biochemistry
California State University, Northridge
Northridge, California, 91330-8262

telephone: (818) 677-3368
e-mail:
thomas.minehan@csun.edu
fax: (818) 677-4068

Office: Eucalyptus 2314

Lab: Eucalyptus 2324-2325


EDUCATION

  • B.A., Columbia University, 1992
  • Ph.D., Harvard University, 1998

POSTDOCTORAL APPOINTMENT

  • California Institute of Technology, 1999-2001

COURSES TAUGHT

  • Chemistry 102, General Chemistry II
  • Chemistry 333, Principles of Organic Chemistry I
  • Chemistry 334, Principles of Organic Chemistry II
  • Chemistry 531, Survey of Organic Reactions
  • Chemistry 534, Advanced Organic Chemimstry

RESEARCH INTERESTS

Organic Chemistry
Research in the Minehan laboratory is focused primarily in two areas: development of synthetic methodology directed toward the preparation of biologically-active natural products, and the development of environmentally-friendly reactions for organic synthesis. We have recently discovered that organoindium compounds serve as efficient reagents for carbon-carbon bond-formation (both in the presence and absence of transition-metal catalysts), even in protic solvents. We would like to further investigate the reactivity of the organometallic intermediates generated upon single-electron transfer from indium species to organic substrates in aqueous media. Furthermore, we have embarked on a detailed study of the reactivity of 1-alkynyl ethers and their utility for forming multiple carbon-carbon bonds in a single synthetic operation. It is hoped that these studies will lead to new and efficient cyclopentannulation strategies. Finally, using the above methodologies, we are developing a practical approach to the terpenoid natural products Dactylol and Xerantholide through investigation of model studies on formation of fused 7-5 and 8-5 carbocyclic ring systems.


REPRESENTATIVE PUBLICATIONS

  1. "Low-Temperature n-Butyllithium-Induced [3,3]-Sigmatropic Rearrangement/ Electrophile Trapping Reactions of Allyl-1,1-Dichlorovinyl Ethers. Synthesis of beta-, gamma- and delta-lactones" Christopher, A.; Brandes, D.; Kelly, S.; Minehan, T.G. Org. Biomol. Chem. (2013), 11, 7658-7661.

  2. "Anti-Peroxyl Radical Quality and Antibacterial Properties of Rooibos Infusions and Their Pure Glycosylated Polyphenolic Constituents" Simpson, M.J.; Hjelmqvist, D.; Karamehmedovic, N.; Minehan, T.G.; Yepremyan, A.; Salehani, B.; Lissi, E.; Joubert, E. Udekwu, K.I.; Alarcon, E.I. Molecules (2013), 18, 11264-11280.

  3. "Lewis-acid catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates" Tran, V.; Minehan, T.G. Org. Lett. (2012), 14, 6100-6103.

  4. "Total Synthesis of Indole-3-acetonitrile-4-methoxy-2-C-beta-D-gluco-pyranoside. Proposal for structural revision of the natural product" Yepremyan, A.; Minehan, T.G. Org. Biomol. Chem. (2012), 10, 5194-5196.

  5. "Intramolecular [2 + 2] Cycloaddition Reactions of Alkynyl Ether Derived Ketenes. A Convenient Synthesis of Donor–Acceptor Cyclobutanes" Tran, V.; Minehan, T.G. Organic Letters (2011), 13, 6588-6591.

  6. "[3,3]-Sigmatropic Rearrangement/5-Exo-Dig Cyclization Reactions of Benzyl Alkynyl Ethers: Synthesis of Substituted 2-Indanones and Indenes" Tudjarian, A.A.; Minehan, T.G. J. Org. Chem. (2011), 76, 3576-3581.

  7. "Indium-Mediated Allylation of Aldehydes, Ketones, and Sulfonimines with 2-(Alkoxy)allyl bromides" Dhanjee, H.; Minehan, T.G. Tetrahedron Lett. (2010), 51, 5609-5612.

  8. "Concise Total Syntheses of Aspalathin and Nothofagin" Yepremyan, A.; Salehani, B.; Minehan, T. G. Organic Letters (2010), 12, 1580-1583.

  9. "A Sequential Indium-Mediated Aldehyde Allylation/Palladium-Catalyzed Cross-Coupling Reaction in the Synthesis of 2-Deoxy-?-C-Aryl Glycosides" Moral, J. A.; Moon, S. -J.; Rodriguez-Torres, S.; Minehan, T. G. Organic Letters (2009), 11, 3734-3737.

  10. "Synthesis of Alkynyl Ethers and Low Temperature Sigmatropic Rearrangement of Ally and Benzyl Alkynyl Ethers" Sosa, J. R.; Tudjarian, A. T.; Minehan, T. G. Organic Letters (2008), 10, 5091-5094.

  11. "Palladium-Catalyzed Reactions of Arylindium Reagents Prepared directly from Aryl Iodides and Indium Metal" Papoian, V.; Minehan, T. G. Journal of Organic Chemistry (2008), 73, 7376-7379.

  12. "An Environmentally Benign Synthesis of cis-2,6-Disubstituted Tetrahydropyrans via Indium-Mediated Tandem Allylation / Prins Cyclization Reaction" Pham, M.; Allatabakhsh, A.; Minehan, T. G. J. Org. Chem. (2008), 73, 741-744.

  13. "Synthesis of Oxa-Bridged 7- and 8-Membered Rings Via Indium-Mediated Annulation of 1,4- and 1,5-Dicarbonyl Compounds with 3-Iodo-2-[(trimethylsilyl)methyl]propene" Allatabakhsh, A.; Pham, M.; Minehan, T. G. Heterocycles (2007), 72, 115-122.

  14. "Palladium-Catalyzed Reactions of Acetoxyenynes with Triorganoindium Reagents" Metza, J. T.; Terzian, R. A.; Minehan, T. G. Tetrahedron, (2006), 47, 8905-8910.

  15. “Low-Temperature n-Butyllithium-Induced Rearrangement of Allyl 1,1-Dichlorovinyl Ethers,” Christopher, A., Brandes, D., Kelly, S., Minehan, T. G. Organic Lett., (2006), 8, 451-454.

LINKS

DR. MINEHAN'S RESEARCH PAGE

DR. MINEHAN'S TEACHING PAGE