John D. Spence

Welcome!

Courses::Research Interests::Publications::Links

Courses ::

• CHEM 25 Organic Chemistry Laboratory (Fall 2008)
• CHEM 124 Organic Chemistry Lecture II (Fall 2008)
•      ch 12 lecture   ch 13 lecture
• CHEM 24 Organic Chemistry Lecture I (Spring 2008)
• CHEM 125 Advanced Organic Chemistry Lab (Spring 2008)
• CHEM 128 Organic Synthesis (Spring 2008)

Research Interests ::

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

1.  Design and Synthesis of Light Activated Enediyne Pro-Drugs.  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 the 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 to improve DNA binding.  In addition, we are exploring methods to improve photochemical activation of the enediyne unit.  Some of the compounds we have synthesized are illustrated below.

2.  Synthesis of Azacalix[4]arenes.  We are 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.  The general structure of the azacalix[4]arene, in it's anticipated cone conformation, is shown below.

Publications ::  Full CV
(undergraduate co-authors underlined)

17.  A. R. Urbach, C. J. Pursell, and J. D. Spence.  Supramolecular Chemistry:  A Senior Capstone Course.  J. Chem. Ed. 2007, 84, 1785-1787.

16.  J. D. Spence, A. E. Hargrove, H. L. Crampton, and D. W. Thomas.  Porphyrenediynes:  Synthesis and Cyclization of meso-Enediynylporphyrins.  Tetrahedron Lett. 2007, 48, 725-728.

15.   N. S. Mills, J. D. Spence and M. M. Bushey.  Capillary Electrophoresis Analysis of Substituted Benzoic Acids.  J. Chem. Ed. 2005, 82, 1226-1228.

14.  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.

13.  T. D. Lash, M. A. Muckey, M. J. Hayes, D. Liu, J. D. Spence and G. M. Ferrence.  Regioselective Oxidation of Benzocarbaporphyrins with Ferric Chloride: A Facile Synthesis of Bridged [18]Annulene Ketals with Strong Absorptions in the Far Red and an Unexpected Halogenation Reaction at the Interior Carbon Atom.  J. Org. Chem. 2003, 68, 8558-8570.

12.  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.

11.  T. D. Lash, M. J. Hayes, J. D. Spence, M. A. Muckey, G. M. Ferrence and L. F. Szczepura.  Conjugated Macrocycles Related to the Porphyrins.  21.  Synthesis, Spectroscopy, Electrochemistry and Structural Characterization of Carbaporphyrins.  J. Org. Chem. 2002, 67, 4860-4874.

10.  T. D. Lash, M. L. Thompson, T. M. Werner and J. D. Spence.  Synthesis of Novel Pyrrolic Compounds from Nitroarenes and Isocyanoacetates Using a Phosphazene Superbase.  Synlett 2000 (2), 213-216.

9.  J. D. Spence and T. D. Lash.  Porphyrins with Exocyclic Rings.  Part 14.  Synthesis of Tetraacenaphtho-porphyrins, a New Family of Highly Conjugated Porphyrins with Record Breaking Long Wavelength Electronic Absorptions.  J. Org. Chem. 2000, 65,1530-1539.   

8.  D. K. Moss, J. D. Spence and M. H. Nantz.  Effects of Propargylic Substitution and Annelation on the Cycloaromatization of a Bicyclo[7.3.1] Enediyne.  J. Org. Chem. 1999, 64, 4339-4343.

7.  T. D. Lash, J. L. Romanic, M. J. Hayes and J. D. Spence.  Towards Hydrocarbon Analogues of the Porphyrins:  Synthesis and Spectroscopic Characterization of the First Dicarbaporphyrin.  J. Chem. Soc., Chem. Commun. 1999, 819-820.

6.  M. J. Hayes, J. D. Spence, and T. D. Lash.  Facile Oxidation of a Carbaporphyrin at the Internal Carbon Atom:  Synthesis of Novel Benzo[18]annulene Ketals.  J. Chem. Soc., Chem. Commun. 1998, 2409-2410.

5.  T. D. Lash, P. Chandrasekar, A. T. Osuma, S. T. Chaney, and J. D. Spence.  Porphyrins with Exocyclic Rings.  Part 13.  Synthesis and Spectroscopic Characterization of Highly Modified Porphyrin Chromophores with Fused Acenaphthylene or Benzothiadiazole Rings.  J. Org. Chem. 1998, 63, 8455-8469.

4.  M. H. Nantz, D. K. Moss, J. D. Spence, and M. M. Olmstead.  Actuating Cycloaromatization of a Bicyclo[7.3.1] Enediyne by Annelation, an Example of Inverse Dependence on Bridge Hybridization.  Angew. Chem. Int. Ed. Engl. 1998, 37, 470-473.

3.  R. P. Balasubramaniam, D. K. Moss, J. K. Wyatt, J. D. Spence, A. Gee, and M. H. Nantz.  Methylation-Ring Opening of 3,3-Disubstituted 2,3-Epoxy Alcohols.  Synthesis of Chiral Quaternary Fragments for Assembly of Briaran Diterpenes.  Tetrahedron 1997, 53, 7429-7444.

2.  J. D. Spence, J. K. Wyatt, D. M. Bender, D. K. Moss and M. H. Nantz.  Stereogenic Propargylic Centers Via Base-Mediated Terminal Allene Isomerization.  J. Org. Chem. 1996, 61, 4014-4021.

1.  J. D. Spence, L. E. Lowrie and M. H. Nantz.  Cyclobutene Formation Accompanying an Intramolecular Lewis Acid-Promoted Spirocyclization of a Propargylic Silane.  Tetrahedron Letters 1995, 36, 5499-5502.

Links ::

RESEARCH

• American Chemical Society
• ACS Publications
• CSUPERB
• Dreyfus Foundation
• Fisher Scientific
• Sigma Aldrich
• VWR
• Porphyrin.Net
• Chemistry Departments in United States

COURSES

• McMurry Text Website
• Spectroscopy Database
• The Basics of NMR
• ChemFinder