John D. Spence

Assistant Professor
Trinity University, Department of Chemistry
715 Stadium Drive, San Antonio, TX  78212
(210)-999-7660  FAX (210)-999-7569
Email:  john.spence@trinity.edu

Education:

Ph. D., Chemistry.  University of California, Davis.  September 1997.
Design and Synthesis of Spirocyclic Supported Enediynes as Calicheamicinone Analogs: Steric Inhibition as a Means to Control Bergman Cycloaromatization.

B. S., Chemistry.  St. Mary's College of California.  May 1992.

Academic Positions:

Assistant Professor, Trinity University, Fall 1999 - Present.
Visiting Assistant Professor, Illinois State University, Fall 1997 - Spring 1999.
 Lecturer, Chemistry Department, UC Davis, Spring 1997.
 Lecturer, Saint Mary's College, Spring 1997.

Research Experience:

Current Research Interests, Trinity University.
Synthesis of porphyrin-enediyne hybrids that utilize unique properties of porphyrin macrocycles to control Bergman cyclization of acyclic enediynes.  Synthesis of nitrogen-bridged macrocycles related to the calixarenes and porphyrins.

Dreyfus Postdoctoral Fellowship, Illinois State University, 8/97 - 8/99.
Synthesized porphyrins with exocyclic rings and investigated what effect these rings have on the porphyrin chromophore; prepared conjugated macrocycles related to the porphyrins wherein one of the interior nitrogen atoms was substituted with a carbon atom and determined new properties; combined these two effects towards the syntheses of porphyrins with long wavelength absorbances.

Doctoral Research, University of California, Davis, 9/92 - 7/97.
Developed methodology for the stereoselective base-mediated isomerization of terminal allenes to terminal alkynes; discovered and optimized novel synthesis of a highly strained cyclobutene; designed and conducted synthesis of spirocyclic analogs of calicheamicinone.

Professional Societies and Organizations:

American Chemical Society
Council for Undergraduate Research
Society of Porphyrins and Phthalocyanines

Awards:

Montalbano Distinguished Professor of the Year, Trinity University Association of Student Representatives, 2001 - 2002
Professor of the Month, Trinity University Association of Student Representatives, October 2001
Dreyfus Fellow, Illinois State University, August 1997 - August 1999.
Teaching Award for Outstanding Graduate Student, UC Davis, May 1997.

Grants Awarded

4.    Petroleum Research Fund, American Chemical Society, “Azacalix[4]arenes:  Nitrogen-Bridged Analogs of p-tert-Butylcalix[4]arene”, $35,000 (2002 – 2004)

3.    Merck Company Foundation AAAS, “Collaborative Research In Chemistry and Biology”, $60,000 (spread between three research groups, 2002 – 2005)

2.    Research Corporation, “Design of Enediyne Pro-Drugs Incorporating Porphyrin Macrocycles as Delivery Agents and Triggering Mechanisms”, $35,000 (2001 – 2003)

1.    Dreyfus Foundation, New Faculty Start-Up Award, $10,000 (2000 – 2002)

Publications:  Undergraduate Co-authors Underlined

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.

Presentations

14.   J. D. Spence.  "Porphyrenediynes:  Synthesis and Bergman Cyclization of Porphyrin-Enediyne Hybrids."  Presented at the 58th Southwest Regional Meeting of the American Chemical Society, Austin, Texas, November 2002.  Paper 361.

13.    J. D. Spence.  "Fragment Approach Towards the Synthesis of Azacalix[4]arenes via Condensations of N-Arylhydroxylamines."  Presented at the 58th Southwest Regional Meeting of the American Chemical Society, Austin, Texas, November 2002.  Paper 205.

12.   J. D. Spence.  “Synthesis and Condensations of N-Arylhydroxylamines for the Preparation of Nitrogen Bridged Calixarenes and Porphyrins.”  Presented at the 57th Southwest Regional Meeting of the American Chemical Society, San Antonio, Texas, October 2001.  Paper 55.

11.   J. D. Spence.  “Nitrogen Bridged Macrocycles Related to Calixarenes.”  Presented at the 37th National Organic Symposium, Bozeman, Montana, June 2001.  Paper 201.

10.   J. D. Spence and T. D. Lash.  “Carbaporphyrins:  Continued Development in the Chemistry of Cyclopentadienyl Analogues of Porphyrins.”  Presented at the 1st International Conference on Porphyrins and Phthalocyanines, Dijon, France, June 2000.  Paper 572.

9.    J. D. Spence, M. J. Hayes, T. D. Lash.  “Synthesis of Carbaporphyrins and Functionalization of the Interior Carbon Atom.”  Presented at the 215th National Meeting of the American Chemical Society, Boston, MA, August 1998.  Paper 728.

8.    J. D. Spence and T. D. Lash.  “Synthesis of Acenaphthoporphyrins:  Extending the Conjugation of the Porphyrin Core to Produce Red-Shifted Spectra.” Presented at the 12th International Conference on Organic Synthesis, Venice, Italy, July 1998.  Paper 063.

7.    J. D. Spence and T. D. Lash.  “Synthesis of Tetraphenyltetraacenaphthoporphyrins.”  Presented at the 31st Great Lakes Regional Meeting of the American Chemical Society, Milwaukee, WI, June 1998.  Paper 189.

6.    J. D. Spence, D. K. Moss, and M. H. Nantz.  "Synthesis of a Bicyclo[7.3.1] Enediyne Equipped with Functionality for Triggering Cycloaromatization."  Presented at the 35th National Organic Chemistry Symposium, San Antonio, TX, June 1997.  Paper 138.

5.    D. K. Moss, J. D. Spence, and M. H. Nantz.  "Synthesis and Triggering of a Spirocyclic Calicheamicinone Analog."  Presented at the 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997.  Paper 98.

4.    J. D. Spence and M. H. Nantz.  "Progress Toward the Synthesis of a Spirocyclic Model of Calicheamicinone."  Presented at the 11th International Conference on Organic Synthesis, Amsterdam, The Netherlands, July 1996.  Paper 387.

3.    J. D. Spence and M. H. Nantz.  "Synthesis of Spirocyclic Supported Enediynes as Calicheamicin Analogs."  Presented at the 8th meeting on Recent Advances in Organometallic Chemistry in Organic Synthesis, Davis, CA, August 1995.  Paper Inv-25.

2.    J. D. Spence and M. H. Nantz.  "Cyclobutene Formation Via Intramolecular Lewis Acid Promoted Conjugate Addition of a Propargyl Silane."  Presented at the 30th Western Regional Meeting of the American Chemical Society, Sacramento, CA, October 1994.  Paper 231.

1.    J. D. Spence and S. J. Bachofer.  "Oxidation Kinetics of an Organic Sulfide Under Micellar Catalysis."  Presented at the Undergraduate Research Symposium, sponsored by the California Section of the American Chemical Society, Moraga, CA, April 1992.

Undergraduate Research Advisees

Dave Oldham, Hannah Heilveil, Amanda Hargrove, Patrick O’Toole, Domingo Llagostera, Erika Garcia, Suhada Ratnayake, Colin Oliver, Jack McKown, Adam Dennis, Brandon Chance, Monica Dyer, Ashley Raymond, Joseph Karam, Sara Hargreaves, David Thomas, Ken Hettie, Eric Cline, Dianne Norton, Jeffrey Grunes, Thomas Pillow, Phuong-Chi Phan, Jason Yoder, Jared Manley, Melanie Muckey, Jennifer Romanic, Michelle Thompson

Undergraduate Presentations

15.   Mandy Hargrove, Hannah Heilveil and John D. Spence.  "Synthetic Approaches Towards Acyclic Enediyne Hybrids."  Presented at the 58th Southwest Regional Meeting of the American Chemical Society, Austin, TX, November 2002, poster 36.

14.   Patrick O'Toole and John D. Spence.  "Synthesis of Conjugated Porphyrin-Enediyne Hybrids."  Presented at the 58th Southwest Regional Meeting of the American Chemical Society, Austin, TX, November 2002, poster 38.

13.   Domingo LLagostera and John D. Spence.  "Synthesis and Reduction of 2-Nitropyrroles."  Presented at the 58th Southwest Regional Meeting of the American Chemical Society, Austin, TX, November 2002, poster 39.

12.   David Thomas and John D. Spence.  “Synthesis of Acyclic Enediyne Diporphyrin Models.” Presented at the 223rd National Meeting of the American Chemical Society, Orlando, FL, April 2002, poster 816.

11.   Eric Cline and John D. Spence.  “Synthesis of Conjugated Porphyrin-Enediyne Hybrids.”  Presented at the 223rd National Meeting of the American Chemical Society, Orlando, FL, April 2002, poster 821.

10.   David Thomas, Colin Oliver and John D. Spence.  “Utilizing Porphyrins to Control Bergman Cyclization of Acyclic Enediynes.”  Presented at the 57th Southwest Regional Meeting of the American Chemical Society, San Antonio, TX, October 2001, poster 286.

9.    Ashley Raymond, Brandon Chance and John D. Spence.  “Synthesis of Azacalixarenes.”  Presented at the 57th Southwest Regional Meeting of the American Chemical Society, San Antonio, TX, October 2001, poster 289.

8.    David Thomas, Colin Oliver and John D. Spence.  “Utilizing Porphyrins to Control Bergman Cyclization of Acyclic Enediynes.”  Presented at the 14th Annual Baylor Undergraduate Research Symposium, Waco, Texas, October 2001.  Also Presented at the 2nd Rice Undergraduate Research Symposium, Houston, Texas, November 2001.

7.    Eric Cline and John D. Spence.  “Porphyrenediyne Hybrids: Conjugation of Enediynes to Porphyrin Macrocycles for Improved Photochemical Activation.”  Presented at the 14th Annual Baylor Undergraduate Research Symposium, Waco, Texas, October 2001.  Also Presented at the 2nd Rice Undergraduate Research Symposium, Houston, Texas, November 2001.

6.    Ashley Raymond and John D. Spence.  “Synthesis of Azacalixarenes.”  Presented at the 14th Annual Baylor Undergraduate Research Symposium, Waco, Texas, October 2001.  Also Presented at the 2nd Rice Undergraduate Research Symposium, Houston, Texas, November 2001.

5.    M. L. Thompson, J. D. Spence, and T. D. Lash.  “Synthesis of Porphyrins with Fused Fluoranthene and Chrysene Subunits.” Presented at the Undergraduate Research Poster Session at the 215th National Meeting of the American Chemical Society, Boston, MA, August 1998.  Paper 256.

4.    J. L. Romanic, J. D. Spence, and T. D. Lash.  “Synthesis of a Dicarbaporphyrin.” Presented at the Undergraduate Research Poster Session at the 215th National Meeting of the American Chemical Society, Boston, MA, August 1998.  Paper 257.

3.    J. L. Yoder, J. D. Spence, and T. D. Lash.  “Improved 2+2 Synthesis of Cycloalkano-porphyrins.” Presented at the Undergraduate Research Poster Session at the 215th National Meeting of the American Chemical Society, Boston, MA, August 1998.  Paper 255.

2.    J. M. Manley, J. D. Spence, and T. D. Lash.  “Synthesis of a Tetranaphthoporphyrin.” Presented at the Undergraduate Research Poster Session at the 215th National Meeting of the American Chemical Society, Boston, MA, August 1998.  Paper 258.

1.    P.-C. Phan, J. D. Spence, and T. D. Lash.  “Synthesis of 21,21-Dithiaporphyrins.” Presented at the Undergraduate Research Poster Session at the 215th National Meeting of the American Chemical Society, Boston, MA, August 1998.  Paper 259.

Undergraduate Student Research Awards

 Hannah Heilveil, Second Place Presentation Rice University Undergraduate Symposium 2003
 Mandy Hargrove, Goldwater Scholarship, 2003-2004
 David Thomas, Merck UNCF Scholarship, $35,000 towards senior year tuition, (2002-2003)
 David Thomas, ACS Organic Division Travel Award, 223rd National Meeting (2002)
 David Thomas, Third Place Presentation Rice University Undergraduate Symposium (2001)

Trinity University Chemistry Majors Advised in Undergraduate Research

Entry

Student

Dates

Post-Graduation

15

Adam Dennis

5/01 – present

2004

14

Amanda Hargrove

1/02 - present

2004

13

Hannah Heilveil

5/02 - present

2004

12

Domingo LLagostera

9/01 - present

2004

11

Patrick O’Toole

9/01 – 5/03

2003:  MD Anderson Biomedical research

10

Suhada Ratnayake

5/01 – 7/01

2003:  Medical School

9

David Thomas

5/00 – 5/03

2003:  Merck Pharmaceutical

8

Eric Cline

1/00 – 5/02

2002:  Merck Pharmaceutical

7

Erika Garcia

9/01 – 5/02

2002:  Chemical Industry

6

Ken Hettie

1/00 – 5/01

2002:  Law school

5

Joseph Karam

9/01 – 12/01

2002:  Medical School

4

Colin Oliver

5/01 – 7/01

2002:  Ph.D., Pharmacology, Roswell Park

3

Diane Norton

9/99 – 9/00

2001:  Admissions Officer, Trinity University

2

Jeff Grunes

9/99 – 5/00

2000:  Ph.D., Chemistry, UC Berkely

1

Tom Pillow

9/99 – 5/00

2000:  Ph.D., Chemistry, Stanford

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