Dr. John Spence

BS Chemistry, Saint Mary’s College of California, 1992

Ph D Chemistry, University of California, Davis, 1997

Chem 24, 124 – Organic Chemistry I and II Lecture
Chem 25 – Organic Chemistry Laboratory
Chem 125 – Advanced Organic Chemistry Laboratory
Chem 128 – Organic Synthesis
Chem 240 – Advanced Instrumentation Laboratory

Research in my group is centered around two general areas in synthetic organic chemistry: (1) the synthesis and activation of enediyne pro-drugs and (2) the synthesis and properties of macrocycles related to porphyrins and calixarenes. 

The Bergman cyclization of enediynes to produce 1,4-phenyl diradicals is an attractive mode of action to cleave DNA.  This cyclization may be initiated thermally or photochemically to produce a benzenoid diradical which is followed by hydrogen atom abstraction from the sugar backbone of DNA leading to strand scission and cell death. We are currently developing enediyne pro-drugs that are fused to heteroaromatic ring systems including porphyrins to improve DNA binding.  In addition, we are exploring methods to improve photochemical activation of the enediyne unit by extending conjugation to the enediyne chromophore.

We are also interested in fine-tuning the properties of calixarenes by developing synthetic methods to systematically replace the bridging carbon atoms in these macrocycles with nitrogen atoms.  This substitution can have a profound effect on the electronic and physical properties of these macrocycles and offer new motifs for their functionalization.

Publications

K. V. Lawson, A. C. Barton and J. D. Spence.  Synthesis of Diazacalix[8]arene and Triazacalix[12]arene Methyl Ethers via Intramolecular Aryl Amination.  Organic Letters, 2009, 11, 895-898.
 
A. R. Urbach, C. J. Pursell and J. D. Spence.  Supramolecular Chemistry:  A Senior Capstone Course.  J. Chem. Ed., 2007, 84, 1785-1787.
 
J. D. Spence, A. E. Hargrove, H. L. Crampton and D. W. Thomas.  Porphyrenediynes:  Synthesis and Cyclization of meso-Enediynylporphyrins.  Tetrahedron Letters, 2007, 48, 725-728.

N. S. Mills, J. D. Spence and M. M. Bushey.  Capillary Electrophoresis Analysis of Substituted Benzoic Acids.  J. Chem. Ed., 2005, 82, 1226-1228.
 
J. D. Spence, E. D. Cline, D. M. LLagostera and P. S. O’Toole.  Synthesis and Bergman Cyclization of a beta-Extended Porphyrenediyne.  Chem. Commun., 2004, 180-181.

J. D. Spence, A. E. Raymond and D. E. Norton.  Condensations of N-Arylhydroxylamines for the Preparation of 5,5’-di-tert-butyl-2,2’-dihydroxydiphenylamine.  Tetrahedron Letters, 2003, 44, 849-851.

Presentations

Nadia Korovina, Benjamin F. Gherman and John D. Spence.  "Synthesis and Photoreactivity of 1,2-bis(naphthalene-1-ylethynyl)benzene:  A Combined Experimental and Computational Investigation."  Presented at the 238th National Meeting of the American Chemical Society, Washington D. C., August 2009.  Paper CHED 283.
 
Michael L. Chang and John D. Spence.  "Syntheses and Reactivity of (Naphthalen-2-yl) and (Phenanthren-9-yl)ethynyl Arenediynes."  Presented at the 237th National Meeting of the American Chemical Society, Salt Lake City, UT, April 2009.  Paper CHED 863.
 
Joseph R. Renner and John D. Spence.  "Highly Conjugated Arenediynes:  Synthesis, Structure, and Reactivity of 1,2-bis(2-(Anthracen-9-yl)ethynyl)benzene."  Presented at the 237th National Meeting of the American Chemical Society, Salt Lake City, UT, April 2009.             Paper CHED 775.
 
Kristie A. Rivera and John D. Spence.  "Synthesis of Phenanthro-Fused Quinoxalenediynes to Examine Enediyne Photoreactivity with Visible Light."  Presented at the 235st National Meeting of the American Chemical Society, New Orleans, LA, April 2008.  Paper 494.
 
Heather J. Walker and John D. Spence.  "Synthesis and Photo-Bergman Cyclization of Naphthylethynyl Arenediynes."  Presented at the 235st National Meeting of the American Chemical Society, New Orleans, LA, April 2008.  Paper 363.

J. D. Spence.  “Synthesis and Bergman Cyclization of Highly Conjugated Arenediynes.”  Presented at the 231st National Meeting of the American Chemical Society, Atlanta, GA, March 2006.  Paper 17.

Andro C. Rios and John D. Spence.  “Design and Synthesis of Aryl-Fused Quinoxalenediynes.”  Presented at the 231st National Meeting of the American Chemical Society, Atlanta, GA, March 2006.  Paper 373.

Kenneth V. Lawson and John D. Spence.  “Synthetic Approaches Towards mono-Azacalix[4]arene.”  Presented at the 231st National Meeting of the American Chemical Society, Atlanta, GA, March 2006.  Paper 551.

Miranda L. Lackie and John. D. Spence.  “Synthesis of 1,2-Bis(phenylbutadiynyl)benzene.”  Presented at the 231st National Meeting of the American Chemical Society, Atlanta, GA, March 2006.  Paper 519.

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