7#$"-!* * * * * *.X**** ***6*x*+\ +|-E*-o7* -E+-E-E- -E-E-E-E-E-EDouglass F. Taber

Douglass F. Taber

Department of Chemistry and Biochemistry
University of Delaware
Newark, Delaware 19716

Phone: (302) 831-2433
Fax: (302) 831-6335
E-Mail: taberdf@udel.edu

Home Page: Taber home page.

Position: Professor Appointed: 1993


B.S., Chemistry, Stanford University, 1970;

Ph.D., Organic Chemistry, Columbia University, 1974


American Chemical Society (ACS)

Past Positions:

1982-1984, University of Delaware, Department of Chemistry, Assistant Professor;

1978-1982, Vanderbilt University, Department of Chemistry, Research Assistant Professor;

1977-1982, Vanderbilt University, Department of Pharmacology, Assistant Professor;

1975-1977, Vanderbilt University, Department of Pharmacology, Research Instructor;

1974-1975, University of Wisconsin, Department of Chemistry, Research Associate


My interests are in the development of new methods for organic synthesis, and the application of those methods to the total synthesis of physiologically active natural products. I am especially interested in enantioselective construction of both carbocycles and heterocycles. These interests include both alkaloid synthesis and prostaglandin synthesis. We have expereince in stable isotope labelling, and in pharamceutical synthesis. A major tool in these developments is the use of transition metal mediated organometallic synthesis, using both stoichiometric and catalytic procedures.

We have developed computational methods for organometallics that are very useful for catalyst design.

Other Expertise:

I have served as a consultant in organometallic chemistry and catalysis, and in organic synthesis. I also maintain a very detailed data base for synthetic organic transformations.

National Science Foundation Graduate Fellowship, 1970-1973.

Expert Witness, patent litigation, 1993-1994


reading, writing, speaking; scale: 1 (basic) to 3 (fluent):

German: 1, -, -;

French: 1, -, -


Fellow of the Alfred P. Sloan Foundation, 1983-1987;

Petroleum Research Fund A/C Research Grant, 1991-1993;

"Synthesis of Taxol," National Institutes of Health Research Grant, GM 46762, 1992-1995;

"Structural Investigation of Prostaglandin Conjugates," National Institutes of Health Research Grant, GM 42056, 1993-1996;

Research Grant, Zeneca Pharmaceuticals, 1994

Links to group members

Meagley, R. P.

Herr, R. J.

Pina, R.


Taber, D.F.; Bhamidipati, R.S.; Thomas, M.L. Cascade Cyclization: Synthesis of (+)-Tuberine. J. Org. Chem. 59: 3442, 1994;

Taber, D.F.; Houze, J.B. The 2-Hydroxycitronellols, Convenient Chirons for Natural Products Synthesis. J. Org. Chem. 59:4004, 1994;

Taber, D.F.; Walter, R.; Meagley, R.P. Intramolecular C-H Insertion by an Alkylidene Carbene: Diastereoselective Synthesis of a Taxol A Ring Synthon. J. Org. Chem. 59:6014, 1994;

Taber, D.F.; Louey, J.P.; Wang, Y.; Nugent, W.A.; Dixon, D.A.; Harlow, R.L. Stereoselectivity in Intramolecular Diene Cyclozirconation: A Combined Experimental and Theoretical Approach. J. Am. Chem. Soc. 116:9457, 1994;

Taber, D.F.; Meagley, R.P.Diastereoselectivity in Uncatalyzed Intramolecular C-H Insertion by an Alkylidene Carbene. Tetrahedron Lett. 35: 7909, 1994

Taber, D.F.; Rahimizadeh, M. Hexasubstituted benzenes by alkyne cyclotrimerization. Tetrahedron Lett. 35: 9139, 1994.

Taber, D.F.; You, K. New synthon for the convergent construction of skipped conjugation polyenes: Synthesis of Ethyl Docosa-4,7, 10, 13, 16, 19-hexaenoate. J. Org. Chem. 60: 139, 1995. 79. Taber, D.F.; Yet, L.; Bhamidipati, R.S. Conversion of phenyldimethylsilyl to the hydroxyl in the presence of a carbon-carbon double bond. Tetrahedron Lett. 36: 351, 1995. 80. Taber, D.F.; Rahimizadeh, M.; You, K.K. Enantioselective synthesis of the Dendrobatid alkaloid (-)-Indolizidine 207A. J. Org. Chem. 60: 529 (1995). 81. Taber, D.F.; You, K.; Song, Y. A simple preparation of a-diazo esters. J. Org. Chem. 60: 1093 (1995). 82. Taber, D.F.; Song, Y. 2,3,5-Trisubstituted tetrahydrofurans by Rh-mediated cyclization of an a-diazo ester. Tetrahedron Lett. 36: 2587 (1995). 83. Taber, D.F.; Gleave, D.M.; Herr, R.J.; Moody, K.; Hennessy, M.J. A new method for the construction of a-diazoketones J. Org. Chem. 60: 2283 (1995). 84. Taber, D.F.; Louey, J. P. 1,2-Induction in intramolecular diene cyclozirconation: Control of relative configuration. Tetrahedron 51: 4495 (1995). 85. Taber, D.F.; You, K. Highly diastereoselective cyclopentane construction: Enantioselective synthesis of the dendrobatid alkaloid 251F J. Am. Chem. Soc. 117: 5757 (1995). 86. Taber, D.F.; Wang, Y. Synthesis of (1,2-13C)-2-chloroethyl phenyl sulfide. J. Labelled. Cmpds. and Radiopharm. XXXVI: 655 (1995). 87. Taber, D.F.; Bhamidipati, R.S.; Yet, L. Phenyldimethylsilyl as an alcohol surrogate in intramolecular Diels-Alder cycloaddition: Synthesis of a-dictyopterol. J. Org. Chem. 60: 5537 (1995). 88. Taber, D.F.; Wang, Y. Kinetic vs. thermodynamic control in intramolecular diene cyclozirconation: Synthesis of elemol. Tetrahedron Lett. 36: 6639 (1995). 89. Taber, D.F.; Meagley, R.P.; Louey, J.P.; Rheingold, A.L. Molecular complex design: Bridging the tetrakiscarboxylatodirhodium core. Inorg. Chim. Acta. 239: 25 (1995). 90. Taber, D.F.; Sahli, A.; Yu, H.; Meagley, R.P. Efficient intramolecular C-H insertion by an alkylidene carbene generated from a vinyl chloride. J. Org. Chem. 60: 6571 (1995). 91. Taber, D.F.; You, K.K.; Rheingold, A.L. Predicting the diastereoselectivity of Rh- mediated intramolecular C-H insertion. J. Am. Chem. Soc. 118: 547 (1996). 92. Yeola, S. N.; Saleh, S.A.; Brash, A.R.; Prakash, C.; Taber, D.F.; Blair, I.A. Synthesis of 10(S)-hydroxyeicosatetraenoic acid: A novel cytochrome P-450 metabolite of arachidonic acid. J. Org. Chem. 61: 838 (1996). 93. Taber, D.F.; Christos, T.E.; Hodge, C.N. Cyclohexenone annelation by alkylidene C-H insertion: Synthesis of oxo-T-cadinol. J. Org. Chem. 61: 2081 (1996). 94. Taber, D.F.; Meagley, R.P.; Supplee, D. A colorful Grignard reaction: Preparation of the triarylmethane dyes from 4-bromo N,N-dimethylaniline. J. Chem. Educ. 73: 259 (1996). 95. Taber, D.F.; Herr, R.J.; Pack, S.K.; Geremia, J.M. A convenient method for the preparation of (Z)-a,b-unsaturated carbonyl compounds. J. Org. Chem. 61: 2908 (1996). 96. Taber, D.F.; Meagley, R.P.; Doren, D.J. Cyclohexenone construction by intramolecular alkylidene C-H insertion: Synthesis of (+)-cassiol. J. Org. Chem. 61: 5723 (1996). 97. Taber, D.F.; Song, Y. Diastereoselective Rh-mediated construction of 2,3,5- trisubstituted tetrahydrofurans. J. Org. Chem. 61: 6706 (1996). 98. Taber, D.F.; Wang, Y., Liehr, S. Mini-scale oxidation/reduction in the organic laboratory course: 4-nitrobenzalehyde / 4-nitrobenzyl alcohol. J. Chem. Educ. 73: 1042 (1996). 99. Taber, D.F.; Song, Y. Stereocontrolled assembly of cis or trans angularly substituted hydrindenes by the unactivated intramolecular Diels-Alder reaction. J. Org. Chem. 61: 7507 (1996). 100. Taber, D.F.; Wang, Y. Synthesis of (-)-haliclonadiamine. J. Am. Chem. Soc. 119: 22 (1997). 101. Taber, D.F.; Herr, R.J.; Gleave, D.M. Diastereoselective synthesis of an isoprostane: ()-8-epi-PG 2 ethyl ester. J. Org. Chem. 62: 194 (1997). 102. Taber, D.F.; Yu, H. Synthesis of a-necrodol: Unexpected formation of a cyclopropene J. Org. Chem. 62: 1687 (1997). 103. Taber, D.F.; Morrow, J.D.; Roberts, L.J.II A nomenclature system for the isoprostanes. Prostaglandins. 53: 63 (1997).


Chemical Synthesis; Drug Design; Organometallic Chemistry


organic synthesis; chemical synthesis; synthesis; natural product; natural product synthesis; enantioselective reaction; organometallic compound; organometallic chemistry; catalysis; pharmaceutical design; alkaloid; pharmaceutical synthesis; prostaglandin

Industrial Relevance:

pharmaceutical design;

pharmaceutical synthesis;

process development;

fine organic and specialty organic synthesis

u Hellos, 1982. V. 86, p. 366. 22. Maas, R. L; Taber, D. F.: and Roberts, L. J., II. Quantitative assay of urinary 2,3-dinor thromboxane B2 by GC-MS. Methods in Enzymology, Eds. W. E. Lands and W. L. Smith, New York, NY, Academic Press, 1982. V. 86, p. 592. 23. Taber, D. F.: TLC mesh column chromatography. Y\DEeg}~46qw8:AC^_QRln~  """ @@M5qrw CD]}~HGH`2 % U V W n  X 2 b c k    {|ijvwFGJK !/ ! ! !!!!URS~23$%  !"""8"O"l"""" ! ! !/!!!*  !@"< y!r!oRPHf!""*X*****: HH@ R*(,, g `d' =/B@H-:LaserWriter 300/LS ChicagoNew YorkGenevaMonacoPalatinoTimes HelveticaCourierSymbolDingbats3278Std3278APL 3278StdBold 3278APLBold3278ALA 3278ALABold Book AntiquaMonotype Sorts WingdingsFootnote*XKlang MT*Script MT Bold*Old English Text MT*New Berolina MT*Bodoni MT Ultra Bold*Arial MT Condensed Light:Gill Sans Condensed Bold((4!!"" Computer Lab Computer Lab