Contact Information
Mail:    Department of Chemistry                            Phone:    (304) 293-3435 ext 4445
          West Virginia University                               FAX:       (304) 293-4904
          P.O.Box 6045
          Morgantown, WV  26506-6045                    email:       kbrummon@wvu.edu

Biographical Sketch

    Kay Michille Brummond (Curriculum vita) was born in the frozen northern tundra of Nebraska.  She received her undergraduate degree at the University of Nebraska, Lincoln (GO BIG RED!).  She received her Ph.D. from the Pennsylvania State University under the direction of Raymond L. Funk.  Her doctoral thesis was entitled "Synthetic Approaches to the Calicheamicin/Esperamicin Bicyclo[7.3.1]tridecenediyne Ring Core and Sulfones in Organic Synthesis."  On completion of her Ph.D. she moved to the University of Rochester for a post-doctoral position with Robert Boeckman, Jr., were she worked on a retro-Claisen approach to the natural product Methynolide.  She accepted a position as an Assistant Professor of Chemistry at West Virginia University in 1993.  She was awarded tenure and promoted to Associate Professor of Chemistry in 1999.  She also holds the position of Adjunct Associate Professor in the Department of Basic Pharmaceutical Sciences in the School of Pharmacy at West Virginia University.  Her research interests include natural product synthesis, cycloaddition reactions involving allenes, solid phase organic synthesis and the development of new organic methodologies using organometallic reagents.

    We are curently working on the synthesis of several natural products which have shown promise as potential anti-cancer compounds.  Hydroxymethylacylfulvene (HMAF) is currently entering Phase II clinical trials versus a variety of solid tumorous cell lines.  We have recently completed the total synthesis of HMAF and are currently exploring the synthesis of a variety of analogs utilizing solid phase organic synthesis.
 
 

    We are also working on the total synthesis of another anti-cancer compound, Suberosenone. Suberosenone possesses a quadrone like skeleton.  We are utilizing our allenic Pauson-Khand methodology to rapidly create the bridged system while forming the a-methylene cyclopentanone.
 
 

  We have developed a rapid approach to the ingenane skeleton.  This approach should quickly set the “in-out” stereochemistry of the ring fusion.  This strategy is currently being applied to the synthesis of Ingenol.
 
 

    We are also interested in utillizing anti-Bredt imminium ions in cycloaddition strategies to alkaloids.  One example of our work in this area is our approach toward the novel immunosuppressant FR 901483
 
 

1. "Recent Advances of the Pauson-Khand Reaction and Related [2 + 2 + 1] Cycloadditions." Tetrahedron Report Number 7934K. M. Brummond; J.L. Kent  Tetrahedron, 2000, 56, 3263.

2. "A Rapid Synthesis of Hydroxymethylacylfulvene (HMAF) Using the Allenic Pauson-Khand Reaction. A Synthetic Approach to Either Enantiomer of the Illudane Structure." K.M. Brummond*; J. Lu. J. Am. Chem. Soc. 2000, 122, 4915.

3. "An Allenic [2 + 2 + 1] Cycloaddition."K.M. Brummond in Advances in Cycloaddition Chemistry, Volume 6, M. Harmata, Ed., JAI Press, 1999, p. 211.

4.  “An Expiditious Synthesis of the Potent Antitumor Agent, (±)-Hydroxymethylacylfulvene  Using an Allenic Pauson-Khand Type Cycloaddition.”  K.M. Brummond, J. Lu, J. Am. Chem. Soc.  1999, 121, 5087.

5.  “A Solid-Phase Synthesis of BRL 49653.”  K.M. Brummond*;  J. Lu;  J. Org. Chem. 1999, 64, 1723.

6.  “a-Chlorination of Ketones Using p-Toluenesulfonyl Chloride."K. M. Brummond*; K.D. Gesenberg; Tetrahedron Lett.   1999, 40, 2231.

7. "Polymorphism in Myristoylpalmitoylphosphatidylcholine." S. Tristram-Nagle;  Y. Isaacson; Y. Lyatskaya; Y. Liu; K. Brummond; J. Katsaras; J. Nagle. Chem. Phys. Lipids 1999, 100, 101.

8.   “An Intramolecular Allenic [2+2+1] Cycloaddition.”  K.M. Brummond*;  J.L. Kent;  H. Wan J. Org. Chem. 1998, 63, 6535.

9.  “A New Preparation of Alkynes from Vinyl Triflates.”  K.M. Brummond*;  K.D. Gesenberg;   J.L.Kent;  A.D. Kerekes Tetrahedron Lett. 1998, 39, 8613.

10.  “The Allenic Pauson-Khand Cycloaddition.  Dependence in p-Bond Selectivity on Substrate  Structure.”  K.M. Brummond*;  H. Wan Tetrahedron Lett.1998, 39, 931.

11.  “Strategy for the Preparation of Allenes froma,b-Unsaturated and Saturated Ketones via Enol  Phosphates." K.M. Brummond*;  E.A. Dingess;  J.L. Kent  J. Org. Chem.1996, 61, 6096.

12.  "A New Allenic Pauson-Khand Cycloaddition for the Preparation of a-Methylene  Cyclopentenones."  J.L. Kent;  H. Wan;  K.M. Brummond* Tetrahedron Lett. 1995, 36, 2407.

13.  "Facile Intramolecular Carbolithiation Reactions of Alkylthio- and Alkoxyacetylenes by  Stabilized Carbanions.  A Novel Strategy for the Synthesis of Functionalized Carbocycles."  R.L.  Funk;  G.L. Bolton;  K.M. Brummond;  K.E. Ellestad;  J.B. Stallman J. Am. Chem. Soc. 1993,  115,7023.

14.  "Stereoselective Preparation of Vinyl Sulfones by Protodesilylation of Allyl Silanes." R.L.  Funk;  J. Umstead-Daggett;  K.M. Brummond Tetrahedron Lett. 1993, 34, 2867.

15.  "Generation of Ketenes from Carboxylic Acids Using the Mukaiyama Reagent (N-Methyl-2- chloropyridinium Iodide)."  R.L. Funk;  K.M. Brummond;  M.M. Abelman Syn. Lett. 1989, 1,36.

COMING SOON TO A JOURNAL NEAR YOU!

1.  "A Tandem Cationic Aza-Cope Rearrangement/Manich Cyclization Approach to FR-901483 by an Anti-Bredt Iminium Ion."  K.M. Brummond*; J. Lu. In preparation.

2. "A Silicon Tethered Pauson-Khand Cycloaddition." K.M. Brummond, B. Rickards. In preparation.

3. "Chiral a-Methylene Cyclopentenones from Chiral Allenes Using an Intramolecular Allenic Pauson-Khand Type Cycloaddition." K.M. Brummond*; A.D. Kerekes; H. Wan. In Preparation.
 
 

Links to Synthetic Organic Chemistry Research Groups
 

Over 300 links directly to the web pages of most of the synthetic organic groups in the U.S.
 

Meetings

Gordon Research Conference Home Page
 
 

Web Resources

Table of pKa's of Organic Acids
Chemistry Departments at U.S. Universities
 
 
 

Website Last Updated: July 30, 2000