Chemistry and Biochemistry

Thomas Minehan

Thomas Minehan
Professor
Email:
Phone:
(818) 677-3368
Office location:
Eucalyptus 2314
Website:

Biography

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 Chemistry

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. "A single-​flask synthesis of α-​alkylidene and α-​benzylidene lactones from ethoxyacetylene, epoxides​/oxetanes, and carbonyl compounds" Ng, K.; Tran, V.; Minehan, T. Tetrahedron Letters (2016), 57, 415-419.
  2. “Synthesis and DNA binding profile of N-​mono- and N,​N'-​disubstituted indolo[3,​2-​b]​carbazoles” Panesar, H.; Solano, J.; Minehan, T.G.  Organic and Biomolecular Chemistry (2015), 13, 2879-2883.
  3. "Total synthesis of polycarcin V and evaluation of its DNA-binding profile” Cai, X.; Ng, K.; Panesar, H.; Moon, S.-J.; Paredes, M.; Ishida, K.; Hertweck, C.; Minehan, T.G. Org. Lett. (2014), 16, 2962–2965.
  4. “Synthesis of 3,3’-di-O-methyl ardimerin and exploration of its DNA binding properties” Mavlan, M.; Panesar, H.; Yepremyan, A.; Minehan T.G. Org. Lett. (2014), 16, 2212-2215.
  5. "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.
  6. "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. 
  7. "Lewis-acid catalyzed intramolecular condensation of ynol ether-acetals. Synthesis of alkoxycycloalkene carboxylates" Tran, V.; Minehan, T.G. Org. Lett. (2012), 14, 6100-6103. 
  8. "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. 
  9. "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. 
  10. "[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. 
  11. "Indium-Mediated Allylation of Aldehydes, Ketones, and Sulfonimines with 2-(Alkoxy)allyl bromides" Dhanjee, H.; Minehan, T.G. Tetrahedron Lett. (2010), 51, 5609-5612. 
  12. "Concise Total Syntheses of Aspalathin and Nothofagin" Yepremyan, A.; Salehani, B.; Minehan, T. G. Organic Letters (2010), 12, 1580-1583. 
  13. "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. 
  14. "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. 
  15. "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. 
  16. "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. 
  17. "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. 
  18. "Palladium-Catalyzed Reactions of Acetoxyenynes with Triorganoindium Reagents" Metza, J. T.; Terzian, R. A.; Minehan, T. G. Tetrahedron, (2006), 47, 8905-8910. 
  19. “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.

MS THESES

  • Christine Dimirjian, "Towards the Synthesis of Diandraflavone" (2015)
  • Xiao Cai, “Total synthesis of Polycarcin V” (2014)
  • Miran Mavlan, “Synthesis of 3,3’-di-O-methylardimerin and evaluation of its DNA binding profile” (2014)
  • Chikako Omura, “Synthesis of aryl piperidine and aryl aza-sugar compound: Mimics of DNA-intercalating agents” (2012)
  • Samuel Rodriguez-Torres, “Development of a new route for the synthesis of 2-deoxy-C-aryl glycosides" (2010)