Wright State University
College of Science and Mathematics

Department of Chemistry

202 Oelman Hall
(937) 775-2855
chemistry@wright.edu

daniel ketcha, ph.d - vita



DANIEL M. KETCHA
Department of Chemistry
Wright State University
Dayton, OH   45435
(937) 873-3230

ACADEMIC QUALIFICATIONS

1977 B.S. Chemistry, King's College, Wilkes-Barre, PA. 
Undergraduate Research and Teaching Assistant with Professor F.X. Smith.

1984 Ph.D. (Organic Chemistry), Temple University, Philadelphia, PA  1984 THESIS:Some Aspects of Sulfilimine Chemistry:  Part I.  The Reaction of Sulfilimines with Ketenes. Part II. The Oxidation of Sulfilimines. *Graduate Advisor, Professor Daniel Swern, deceased December 5, 1982.

1983-85 Postdoctoral Research Associate and Research Instructor with Professor G. W. Gribble, Dartmouth College, Hanover, NH

1985-91 Assistant Professorship at Wright State University

1991- Associate Professorship at Wright State University

PROFESSIONAL ACTIVITIES AND SERVICE

REVIEWING

1. Referee for the National Science Foundation, ACS Petroleum Research Fund, Journal of       Organic Chemistry, Tetrahedron Letters, Journal of Chemical Education.

2. Ad Hoc Contracts Technical Review Group for National Cancer Institute, August 27-28,1987.  (a) "Master Agreements for the Large Scale Isolation of Anti-AIDS Agents from Natural Sources."  (b) "Synthesis of Congeners and Prodrugs of Anti-AIDS Compounds."

3. National Institutes of Health, National Cancer Institute, July 29-30, 1991 “Analyses and Physiology of Anticarcinogens in Soybeans.”

AMERICAN CHEMICAL SOCIETY

1.    Secretary, Dayton Section, 1987.
2.    Chairman-Elect, Dayton Section, 1988.
3.    Chairman,  Dayton Section, 1989.
4.    Co-Chairman, National Chemistry Week Committee, Dayton Section, 1989.
5.    Immediate Past Chairman, Dayton  Section, 1990.
6.    Co-Chairman, Campaign for Chemistry Committee, Dayton Section, 1990.
7.    Organizer, Student Mentor Interface Workshop, 25th Central Regional Meeting, American       Chemical Society, Pittsburgh, Pennsylvania, October 4-6, 1993.
                                                           

PUBLICATIONS

JOURNAL ARTICLES

1.    Ketcha, D. M., Abou-Gharbia, M., Smith, F. X., Swern, D.  "Reaction of N-Acylsulfilimines with Diphenyl Ketene; A New Synthesis of 2-Oxazolin-4-ones" Tetrahedron Lett.  1983, 24, 2811-2814.

2.    Ketcha, D. M., Swern, D. "Peroxyacetic Acid:  A Useful Coxidant for the Ruthenium Tetroxide Oxidation of N-Sulfonylsulfilimines"  Synth. Commun. 1984, 14 , 915-919.

3.    Abou-Gharbia, M., Ketcha, D. M., Zacharias D. E., Swern, D. "Reaction of Ketenes with Sulfilimines.  Synthetic Routes to Oxazolinones and Indolinones"  J. Org. Chem. 1985, 50, 2224-2228.

4.    Ketcha, D. M., Gribble, G. W.  "A Convenient Synthesis of 3-Acylindoles via Friedel-Crafts Acylation of 1-(Phenylsulfonyl)indole.  A New Route to Pyridocarbazole-5,11-quinones and Ellipticine"  J. Org. Chem. 1985, 50, 5451-5457.

5.    Ketcha, D. M. "The Manganese (III) Acetate Oxidation of N-Protected Indolines" Tetrahedron Lett. 1988, 29, 2151-2154.

6.    Gribble, G. W, Fletcher, G. L., Ketcha, D. M., Rajopadhye, M.  "Metalated Heterocycles in the Synthesis of Ellipticine Analogues.  A New Route to the 10 H-Pyrido[2,3-b]carbazole       Ring System"  J. Org. Chem.  1989, 54, 3264-3269.

7.    Ketcha, D. M., Lieurance, B. A., Homan, D. F. J., Gribble, G. W.  " Synthesis of Alkyl      Substituted N-Protected Indoles via Acylation and Reductive Deoxygenation" J.Org.Chem. 1989, 54, 4350-4356.

8.    Ketcha, D. M., Lieurance, B. A.  "The Reduction of N-(Phenylsulfonyl)indoles with Sodium Cyanoborohydride in Trifluoroacetic Acid" Tetrahedron Lett.  1989, 30, 6833-6836.

9.    Ketcha, D. M., Carpenter, K. P., Atkinson, S. T., Rajagopalan, H. R., "The Reductive Deoxygenation of 2-and 3-Acyl-1 (Phenylsulfonyl)pyrroles" Synth. Commun. 1990, 20, 1647-1655.

10.   Ketcha, D. M., Carpenter, K. P., Zhou, Q.  "The Reduction of N-(Phenylsulfonyl)pyrroles with Sodium Cyanoborohydride in Trifluoroacetic Acid" J. Org. Chem. 1991, 56 1318-  1320.

11.   Grossie, D. A., Ketcha, D. M.  “1-Benzenesulfonyl-3-methyl-2-oxo-2,3-dihydroindol-3-yl Acetate” Acta Cryst.  1992, C48, 1718-1720.

12.   Gribble, G. W., Saulnier, M., Obaza-Nutaitis, J. A., Ketcha, D. M.  “A Versatile and Efficient Construction of the 6H-Pyrido[4,3-b]carbazole Ring System. Syntheses of the Antitumor Alkaloids Ellipticine, 9-Methoxyellipticine, and Olivacine and their Analogues J.Org. Chem. 1992, 57, 5891-5899.

13.   Ketcha, D. M.; Zhou, Q.; Grossie, D.  “Manganese(III) Acetate Oxidation of Alkyl Substituted 1-(Phenylsulfonyl)indoles” Synth. Commun. 1994, 24, 565-574.

MASTERS THESIS

1.    Qin Zhou, "Synthetic Approaches to Natural Products. Part I. Oxidation of Indoles. Part II. Reduction of Pyrroles”, Wright State University, 1990.

2.    Hema R. Rajagopalan, “Synthesis of Dehydroepiandrosterone (DHEA) Derivatives, Wright State University, 1991.

3.    Yongping Xie, “Synthetic Approaches to Ant Venom Alkaloids by the Regioselective Functionalization of 1-(Phenylsulfonyl)pyrrole”, Wright State University, 1991.

4.    Jeffrey A. Schreier, “Parmeters Controlling the Regioselectivity of Friedel-Crafts Acylations of N-(Phenylsulfonyl)pyrrole”, Wright State University, 1992.

5.    Dong Xiao, “Applications of N-Phenylsulfonylpyrrole Chemistry to the Synthesis of Pyrrole and Indole Alkaloids”, Wright State University, 1994.

6.    Brett A. Lieurance, “Synthetic Approaches to the Mitomycin and Ergot Alkaloids”, Wright State University, 1994.

BOOKS

1.    K. Turnbull and D. M. Ketcha, Editors; "Annual Reports in Organic Synthesis-1989", Academic Press (1989)

2.    K. Turnbull, D. M. Ketcha, J. Keay, P. Weintraub, Editors; "Annual Reports in Organic Synthesis - 1990", Academic Press (1990).

3.    Weintraub, P. M., Turnbull, K., Ketcha, D. M., Gross, R., Zhang. T., Editors; “Annual Reports in Organic Synthesis - 1992”, Academic Press (1993).

4.    Weintraub, P.M., Turnbull, K., Ketcha, D. M., Gross, R., Zhang T., Editors; “Annual Reports in Organic Synthesis - 1993”, Academic Press (1994).

SCIENTIFIC PRESENTATIONS

LOCAL

1.    Philadelphia Organic Chemists Club, Poster Session, Drexel University, June 1981; with M. Abou-Gharbia, and D. Swern, "A  New Synthesis of Oxindoles."

2.    8th Regional Cancer Research Symposium, University of Vermont, November 1984; with  G. W. Gribble,  J. A. Obaza-Nutaitis, G. D. Jaycox, and M. G. Saulnier, "Synthesis and Screening of Anticancer Ellipticine Derivatives."

3.    Dayton Section, American Chemical Society, Poster Session, University of Dayton, March      11, 1986; "Approaches to Indole Alkaloids."

4.    5th Annual Science Symposium, Central State University, May 2, 1987; with D. F. J. Homan and K. P. Carpenter, "Sodium Borohydride/Trifluoroacetic Acid for the   Chemoselective Reduction of 3-Acyl-N-Protected Indoles."

5.    5th Annual Science Symposium, Central State University, May 2, 1987; with D. F. J. Homan and R. C. Tomlinson, "Selective Functionalization of Indoles: Approaches to 2      Halogenated Ergot Alkaloids."

6.    Dayton Section, American Chemical Society, Poster Session, University of Dayton, March 8, 1988; with  D. F. J. Homan and B. A. Lieurance,"Silicon Mediated Functionalization of Indoles."

7.    6th Annual Science Symposium, Central State University, May 14, 1988; with  K. P. Carpenter, "Directed Lithiation of Indoles."

8.    6th Annual Science Symposium, Central State University, May 14, 1988; with  B. A. Lieurance, "Silicon Mediated Functionalization of Indoles."

9.    Dayton Section, American Chemical Society, Poster Session, University of Dayton, March 14, 1989; with  B.A. Lieurance, "The Reduction of N-Protected Indoles with Sodium Cyanoborohydride in Trifluoroacetic Acid."

10.   7th Annual Science Symposium, Central State University, May 14, 1988; with  B. A.      Lieurance, "The Reduction of N-Protected Indoles with Sodium Cyanoborohydride in Trifluoroacetic Acid."

11.   Dayton Section, American Chemical Society, Poster Session, University of Dayton, February 15, 1990; with Q. Zhou, "Synthetic Approaches to the Mitomycin Skeleton."

12.   Dayton Section, American Chemical Society, Poster Session, University of Dayton, February 15, 1990; with K.P. Carpenter, S.T. Atkinson and H. Rajogopolan, "Synthetic Approaches to the Indolizidine Alkaloids."

13.   Dayton Section, American Chemical Society, Poster Session, University of Dayton, February 13, 1991; with Y. P. Xie, "Synthesis of Ant Venom Alkaloids from Pyrrole."

14.   Dayton Section, American Chemical Society, Poster Session, University of Dayton, February 13, 1991; with H. R. Rajagopalan, "Drug Targeting Against Breast Cancer."

15.   Dayton Section, American Chemical Society, Poster Session, University of Dayton, February 13, 1991; with J. A. Schreier, "Friedel-Crafts Acylations of Alkyl-1-(Phenylsulfonyl)pyrroles."

16.   Dayton Section, American Chemical Society, Poster Session, University of Dayton, February 4, 1993; with J. H. Cook and J. A. Schreier, “Selective Functionalization of Alkyl Substituted N-(Phenylsulfonyl)pyrroles.”

17.   Dayton Section, American Chemical Society, Poster Session, University of Dayton, February 4, 1993; with S. A. Jones, J. A. Schreier, S. T. Atkinson, “Synthetic Approaches to the Indolizidine Alkaloids from N-(Phenylsulfonyl)pyrrole.”

SCIENTIFIC PRESENTATIONS

NATIONAL/INTERNATIONAL

1.    11th  Middle Atlantic Regional Meeting, American Chemical Society, University of Delaware, Newark, DE, April 1977; with F. X. Smith, "The Acid Catalyzed Rearrangement of Substituted 3-Vinylindoles."

2.    13th  Middle Atlantic Regional Meeting, American Chemical Society, Monmouth College, West Long Branch, NJ, March 1979; with D. Swern, "Peroxyacetic Acid:  A Useful Cooxidant for the Ruthenium Tetroxide Oxidation of N-Aryl-Sulfonylsulfilimines to     Sulfoximines."

3.    181st  Meeting, American Chemical Society,  Atlanta, GA, March 1981; with M. Abou Gharbia and D. Swern, "Reactions of Ketenes with Sulfilimines."
 
4.    10th International Congress of Heterocyclic Chemistry, University of Waterloo, Ontario, Canada, August 1985; with M. Abou-Gharbia,  D.E. Zacharias and D. Swern, "Reactions of Ketenes with Sulfilimines. Synthetic Routes to Oxazolinones and Indolinones."

5.    30th National Organic Symposium, University of British Columbia, Vancouver, B.C., Canada, June 22, 1987; "Selective Functionalization of Indoles."

6.    3rd Chemical Congress of North America, American Chemical Society, Toronto, Ontario, Canada, June 6, 1988; with D. F. Homan, and G. W. Gribble, "The Chemoselective      Reduction of Indolyl Ketones with Sodium Borohydride in Trifluoroacetic Acid."

7.    21st Central Regional Meeting, American Chemical Society, Cleveland, Ohio, May 31, 1989; with B.A. Lieurance, and J. Shidler, "Silicon Mediated Functionalization of Indoles."

8.    Gordon Research Conference on Heterocyclic Compounds, Poster Session, New Hampton School, New Hampton, NH, July 9-14, 1989; with B. A. Lieurance and K. P. Carpenter, "The Reduction of N-Protected Indoles and Pyrroles with Sodium Cyanoborohydride in Trifluoroacetic Acid."

9.    International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, December 20, 1989; with R. C. Tomlinson, K. P. Carpenter and B. A. Lieurance, "Reduction of N      Protected Indoles with Sodium Cyanoborohydride in Trifluoroacetic Acid."

10.   22nd Central Regional Meeting, American Chemical Society, Saginaw, Michigan, June 8, 1990; with Q. Zhou, "Synthetic Approaches to the Mitomycin Skeleton: the Mn(III) Oxidation of C-Alkylindoles."

11.   22nd Central Regional Meeting, American Chemical Society, Saginaw, Michigan, June 8, 1990; with K. P. Carpenter, S. T. Atkinson and H. R. Rajagopalan, "Synthetic Approaches to the Indolizidine Alkaloids: the Reduction of N-Protected Pyrroles."

12.   201st Meeting, American Chemical Society, Atlanta, GA, April 15, 1991, Division of Chemical Education Symposium on Imaginative Approaches to Student Affiliate Sections; with Becky Grinstead and Timothy Grinstead, "The Student Affiliates at Wright State University."

13.   1991 Joint Central-Great Lakes Regional Meeting, American Chemical Society, Indianapolis, Indiana, May 30, 1991:  with J. A. Schreier, "The Selective Functionalization of Pyrrole."

14.   1991 Joint Central-Great Lakes Regional Meeting, American Chemical Society, Indianapolis, Indiana, May 31, 1991; with H. R. Rajagopalan, "Drug Targeting Against Breast Cancer."

15.   13th International Congress of Heterocyclic Chemistry, Corvallis, Oregon, August 11-16, 1991, with J. A. Schreier and Y. P. Xie, “Synthesis of Natural Products from Pyrrole.”

16.   205th Meeting, American Chemical Society, Denver, Colorado, March 31, 1993; with S. A. Jones, J. A. Schreier, S. T. Atkinson, “Synthetic Approaches to the Indolizidine Alkaloids from N-(Phenylsulfonyl)pyrrole.”

17.   205th Meeting, American Chemical Society, Denver, Colorado, March 31, 1993; with J. H. Cook and J. A. Schreier, “Selective Functionalization of Alkyl Substituted N-      (Phenylsulfonyl)pyrroles.”

18.   205th Meeting American Chemical Society, Denver, Colorado, March 29, 1993; with T. Bornhorst, D. Bland, R. Carlson, M. Griffith, T. Grinstead, C. Schultz, J. Stouffer, D. Dolson and D. Bombick, “How to do Chemistry the Wright Way.”

19.   25th Central Regional Meeting, American Chemical Society, Pittsburgh, Pennsylvania, October 4-6, 1993; with D. A. Smith, “Synthesis of Polysubstituted Pyrroles by the Selective Functionalization of N-(Phenylsulfonyl)pyrroles.  A Rationalization of the Selectivity Patterns.”

20.   25th Central Regional Meeting, American Chemical Society, Pittsburgh, Pennsylvania, October 4-6, 1993; with K. E. Shipp and J. P. Brooke, “Steps in the Wright Direction:  A Sequential Organic Synthesis Puzzle.”

21.   25th Central Regional Meeting, American Chemical Society, Pittsburgh, Pennsylvania, October 4-6, 1993; with J. G. Grieb, J. P. Brooke and J. A. Schreier, “Synthetic Approaches to the Antifungal Alkaloids Anisomycin and Preussin from N-(Phenylsulfonyl)pyrrole.”

22.   25th Central Regional Meeting, American Chemical Society, Pittsburgh, Pennsylvania, October 4-6, 1993; with J. P. Brooke, “Synthesis and Beckmann Rearrangements of Oximes Derived from Acyl-1-(Phenylsulfonyl)pyrroles; Approaches to Distamycin.”

INVITED LECTURES

1.    Miami University of Ohio, Oxford, OH, February 13, 1986; "Reactions of Ketenes with Sulfilimines: Synthetic Routes to Oxazolinones and Indolinones."

2.    Wright State University, Department of Biochemistry, February 26, 1988; "DHEA and Hormone-Dependent Tumors; Prospects for Targeting Cytotoxic Agents."

3.    Monsanto Research Corporation - Mound Laboratory, Miamisburg, OH, April 19, 1988; "New Approaches to Cancer Chemotherapy."

4.    University of Dayton, Dayton, OH, October 18, 1990; "Synthetic Approaches to Antitumor Alkaloids."

5.    Ohio Wesleyan University, Delaware, OH, February 8, 1991; "Synthesis of Natural Products Using N-Substituted Pyrroles."

6.    DePauw University, Greencastle, IN, Novermber 11, 1992; “Steroid Hormones and Human Cancer.”

7.    University of Cincinnati, Cincinnati, OH, February 11, 1993; “Synthesis of Natural Products from N-(Phenylsulfonyl)pyrroles.”

8.    Isotec, Inc., Miamisburg, OH, November 19, 1993, “Selective Functionalization of N-(Phenylsulfonyl)pyrroles.”

GRANTS AND CONTRACTS

1.    WSU Seed Grant, 1986. "Design and Synthesis of Antitumor Agents Directed Towards      Human Breast Cancer." $2,000

2.    American Chemical Society, Petroleum Research Fund, 9/1/86 to 12/31/88. "Synthetic Approaches to 2-Halogenated Ergot Alkaloids."  $18,000

3.    WSU Research Incentive and Research Development Award, 7/1/87 to 12/31/88."Synthesis of Alkaloids Using Indole-2,3-Quinodimethanes."   $1,300.

4.    Research Corporation, 6/30/89 to 6/30/91. "The Selective Functionalization of N-Protected Indoles via Directed Lithiation."  $18,000.

5.    WSU Research Incentive Travel Grant, July, 1989.  $600.

6.    WSU Biomedical Seed Grant, 6/15/90 to 6/15/91. "The Design and Synthesis of Structurally Simple Analogues of the Mitomycin Alkaloids as Potential Bifunctional Alkylating Antitumor Antibiotics."  $762.

7.    WSU Alumni Special Grants Program, 2/22/91 to 12/31/91.  "Chemistry Club Demonstrations."  $1,300.

8.    American Chemical Society, Petroleum Research Fund, 1/1/92 to 8/31/94. "Synthesis of Natural Products Using N-Protected Pyrroles."  $20,000.  

9.    Xiao, D., Ketcha, D. M. “Diels-Alder Reactions of 2- and 3-Vinyl-1-(Phenylsulfonyl)pyrroles” J. Heterocycl. Chem., submitted 10/7/94.

10.   Grieb, J. G., Ketcha, D. M.  “Synthesis of 2-Aryl-1-(Phenylsulfonyl)pyrroles” Synth. Commun., submitted 10/13/94.

11.   WSU Research Challenge Early Start/Augmentation Grant, 7/1/94 to 6/30/95.  “Synthesis of Natural Products Using N-Protected Pyrroles.” $5,000.

 

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