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GEORGE
AUGUSTINE
O'DOHERTY
Associate Professor Department
of Chemistry West
Virginia University Morgantown,
West Virginia 26506 E-mail:
George.ODoherty@mail.wvu.edu Web:
http://www.as.wvu.edu/~odoherty Phone:
(304) 293-3435 (ext. 6444) Fax:
(304) 293-4904
DATE OF BIRTH: August
28, 1966; Kilkenny, Ireland EDUCATION:
The Ohio State University,
Columbus, Ohio Ph.D.,
Chemistry, Sept. 1987 to Jan. 1993 Advisor:
Professor Leo A. Paquette Rensselaer
Polytechnic Institute, Troy, New York B.S.,
Chemistry, Sept. 1984 - June 1987 Advisor:
Professor Alan R. Cutler SCIENTIFIC
EMPLOYMENT: Associate
Professor Chemistry (Aug. 2005 – present) Department
of Chemistry, West Virginia University Assistant
Professor Chemistry (Sept. 2002 – Aug. 2005) Department
of Chemistry, West Virginia University Assistant
Professor Chemistry (Sept. 1996 - 2002) Department
of Chemistry, University of Minnesota I.
C. Postdoctoral Scholar (Sept. 1995 - 1996) Department
of Chemistry, Imperial College, London Advisor:
Professor Anthony G. M. Barrett NSF
Postdoctoral Scholar (Jan. 1993 – Aug. 1995) Department
of Chemistry, Stanford University Advisor:
Professor Barry M. Trost HONORS and
AWARDS: Eberly
College of Arts and Science Outstanding Researcher Award (2007) Woodburn
Professor, Eberly College of Arts and Science (2006 & 2007) WVU’s
Dept. of Chemistry Outstanding Professor (2006) Shanghai
Normal University “Honored Professor” (Dec. 2005) Arnold
and Mabel Beckman Young Investigator (Sept. 1999 to Aug. 2002) NSF
Postdoctoral Fellowship (Jan. 1993 to Dec. 1994) British
Petroleum America Fellowship (Jan. 1991 to Dec. 1991) National
Need Fellowship (Jan. 1989 to Dec. 1989) OSU
Departmental Fellowship (Sept. 1987 to Aug. 1988) American
Chemical Society (1987 to present) PUBLICATIONS:
67. "De Novo Asymmetric Synthesis and Biological Evaluation of the Trisaccharide Portion of PI-080 and Vineomycin B2” X. Yu, G. A. O’Doherty, Submitted. 66. "Synthesis of Cyclitol Sugars via Pd-Catalyzed Cyclopropanol Ring Opening” M. Shan, G. A. O’Doherty, Submitted. 65. "De Novo Asymmetric Approaches To 2-Amino-N-(Benzyloxycarbonyl)-1-(2’-Furyl)-Ethanol And 2-Amino-N-(t-Butoxycarbonyl)-1-(2’-Furyl)-Ethanol” M. Croate, M. H. Haukaas, M. Li, A. M. Starosotnikov, and G. A. O’Doherty, Submitted. 64. "Synthesis of Carbasugar C-1
Phosphates via Pd-Catalyzed Cyclopropanol Ring Opening” M. Shan, G. A.
O’Doherty, Submitted. 63.
"De Novo Asymmetric Synthesis of Anthrax Tetrasaccharide and
Analogue” H.
Guo, G. A. O’Doherty, J. Org. Chem.
2008, ASAP. 62.
"Formal Total Synthesis of RK-397 via an Asymmetric Hydration and
Iterative Allylation Strategy” H.
Guo, M. S. Mortensen, G. A.
O’Doherty, Org.
Lett. 2008, ASAP. 61.
"De Novo Asymmetric Synthesis of the Trisaccharide Subunit of
Landomycin A and E” M. Zhou, G. A. O’Doherty,
Org. Lett. 2008, ASAP. 60.
"Metabolite induction of Caenorhabditis elegans
dauer larvae arises via transport in the pharynx” T. J. Baiga,
H. Guo,
Y. Xing, G. A. O'Doherty, A. Parrish, A. Dillin, M. B. Austin, J. P.
Noel, James J. La Clair, ACS
Chem. Biol.
2008,
3, 294-304. 59.
"De Novo Asymmetric Synthesis of 8a-epi-Swainsonine” J. N. Abrams, R. S. Babu, H.
Guo, D. Le, J. Le, J. M. Osbourn and G. A. O’Doherty, J.
Org. Chem. 2008, 73, 1935-1940. 58.
"De Novo Asymmetric Syntheses of D-, L- and 8-epi-Swainsonine”
H. Guo
and G. A. O’Doherty, Tetrahedron, 2008, 64,
304-313. 57.
"The De Novo Synthesis of Oligosaccharides:
Application to the Medicinal Chemical Study of Digitoxin."
Zhou, M. and O’Doherty, G. A. Current
Topics in Medicinal Chemistry, 2008,
8, 114-125. 56.
"De Novo Formal Synthesis of (–)-Virginiamycin M2 via
the Asymmetric Hydration of Dienoates” M. S. Mortensen, J. M. Osbourn and G.
A. O’Doherty,
Org. Lett. 2007, 9
3105-3108. 55.
"Synthesis of
Aza-Analogues of the Glycosylated Tyrosine Portion of Mannopeptimycin-E.” S.
Guppi and G. A.
O’Doherty,
J. Org. Chem. 2007,
72, 4966-4969.
54. "De Novo Asymmetric Synthesis of the Anthrax Tetrasaccharide via a Palladium Catalyzed Glycosylation Reaction.” H. Guo and G. A. O’Doherty, Angew. Chem. Int. Ed. 2007, 46, 5206-5208. 53.
"De Novo Approach to 2-Deoxy-b-Glycosides:
Asymmetric Syntheses of Digioxose and Digitoxin.”
M.
Zhou
and G. A. O’Doherty,
J. Org. Chem. 2007, 72,
2485-2493. 52.
"De Novo Formal Synthesis of (-)-Apicularen A via
an Iterative Asymmetric Hydration Sequence.”
M. Li and G. A. O’Doherty,
Org. Lett. 2006, 8,
6087-6090. 51. "De
Novo Asymmetric Synthesis of SL0101 and its Analogues via a
Palladium-Catalyzed Glycosylation.” M. Shan and G. A. O’Doherty,
Org. Lett. 2006, 8, 5149-5152. 50.
“A De Novo Asymmetric Approach to Achiral Deoxy-Melodorinol Analogues” Md.
M. Ahmed, N.
Akhmedov, H. Cui, D. Friedrich and G. A. O’Doherty,
Heterocycles, 2006,
70, 223-233. 49. "De
Novo Asymmetric Synthesis of Milbemycin b3 via an Iterative Asymmetric Hydration Approach.”
M. Li and G. A. O’Doherty,
Org. Lett. 2006, 8, 3987-3990. 48. "De Novo
Synthesis of 2-Substituted Syn-1,3-Diols
Via an Iterative Asymmetric Hydration Strategy.” Md. M. Ahmed, M. S. Mortensen
and G. A. O’Doherty,
J. Org. Chem. 2006, 71, 7741-7746. 47.
“De Novo Asymmetric Syntheses of Muricatacin and its Analogues via
Dihydroxylation of Dienoates” Md. M. Ahmed, H. Cui and
G. A. O’Doherty,
J. Org. Chem. 2006, 71, 6686-6689. 46. "De Novo
Asymmetric Synthesis of Digitoxin via a Palladium Catalyzed Glycosylation
Reaction" M. Zhou and G. A.
O’Doherty, Org. Lett. 2006, 8, 4339-4342. 45.
“De Novo Asymmetric Syntheses
of C-4-Substituted Sugars Via an
Iterative Dihydroxylation Strategy”
Md.
M. Ahmed
and G.
A. O’Doherty,
Carbohydr. Res. 2006, 341, 1505-1521. 44.
“Synthetic
Studies Towards Mannopeptimycin-E: Synthesis
of a O-Linked Tyrosine 1,4-a,a-Manno,Manno-Pyanosyl-Pyranoside”
R. S.
Babu, Sanjeeva R. Guppi and G. A. O’Doherty,
Org. Lett. 2006, 8,
1605 - 1608. 43.
“De
Novo Asymmetric Synthesis of D- and L-Swainsonine”
H.
Guo and G. A. O’Doherty,
Org. Lett. 2006, 8, 1609 - 1612. 42.
"De Novo Asymmetric Synthesis of Homo-Adenosine via a Palladium Catalyzed N-Glycosylation" S. R. Guppi, M. Zhou and G. A. O’Doherty, Org.
Lett. 2006, 8, 293-296. 41.
"A
Diastereoselective Silver(I) Promoted Gem-Dibromocyclopropane Ring Opening
Reaction via an Anchimeric Assisted Transannular Benzoate Migration"
M. S. Mortensen, A. C. Schmitt, C. M. Smith, E. A. Voight and G. A. O’Doherty,
Heterocycles, 2006, 67(2),
721-730. Special issue in honor of
Barry M. Trost’s 65th B’day. 40.
"De
Novo Asymmetric Synthesis of Anamarine and Analogs."
D.
Gao
and G. A. O'Doherty, J. Org. Chem. 2005,
70, 9932-9939. 39.
"De
Novo Asymmetric Syntheses of D- and L-Talose via an Iterative Dihydroxylation of
Dienoates."
Md.
M. Ahmed
and G. A. O'Doherty, J. Org. Chem. 2005,
67, 10576 - 10578. 38.
“De
Novo Asymmetric Synthesis of Daumone via a Palladium Catalyzed Glycosylation”
H.
Guo and G. A. O’Doherty,
Org. Let. 2005, 7, 3921-3924. 37.
“Enzymatic Incorporation of Orthoganally Reactive Prenylazide Groups into
Peptides Using Geranylazide Diphosphate Via Protein Farnesyltranserase:
Implications for Selective Protein Labeling” M. W. Rose, J.Xu, T. A.
Kale,
G.
A. O'Doherty
,
G. Barany, M. D. Distefano, Biopolymers
2005, 80, 164-171. 36.
"De
Novo Asymmetric Synthesis of a Galacto-Papulacandin
Moiety Via an Iterative Dihydroxylation Strategy"
Md.
M. Ahmed
and G. A. O'Doherty, Tetrahedron Lett. 2005,
46, 4151-4155. 35.
"Enantioselective
Synthesis of 10-epi-Anammarine via an
Iterative Dihydroxylation Sequence."
D.
Gao
and G. A. O'Doherty, Org. Lett. 2005, 7, 1069-1072. 34.
"Palladium
Catalyzed Glycosylation Reaction: De-Novo
Synthesis of Trehalose Analogues."
R. S.
Babu
and G. A. O'Doherty, J. Carb. Chem. 2005,
24, 169-177. 33.
"Remote
Steric Effect on the Regioselectivity of the Sharpless Asymmetric
Dihydroxylation."
Y.
Zhang
and G. A. O'Doherty, Tetrahedron 2005,
61, 6337–6351. 32.
"
De novo synthesis of galacto-sugar
d-lactones
via a catalytic osmium/palladium/osmium reaction sequence"
Md.
M. Ahmed
and G. A. O'Doherty, Tetrahedron Lett.
2005, 46, 3015-3019. 31.
"De
Novo Enantioselective Syntheses of Galacto-Sugars
and Deoxy-Sugars via the Iterative Dihydroxylation of Dienoate."
Md.
M. Ahmed,
B. P.
Berry, T.
J. Hunter,
D. J. Tomcik and
G. A. O'Doherty, Org. Lett. 2005, 7, 745-748. 30.
"An Enantioselective Synthesis of Phomopsolide D." M. Li, and G. A.
O'Doherty, Tetrahedron Lett. 2004, 45, 6407-6411. 29.
"De-Novo
Synthesis of Oligosaccharides Using a Palladium Catalyzed Glycosylation Reaction."
R. S.
Babu, M. Zhou and G. A. O’Doherty,
J. Am. Chem. Soc. 2004, 126,
3428 - 3429. 28.
"Synthesis of 7-Oxa-Phomopsolide E and Its C-4 Epimer” M. Li, J. G. Scott
and G. A. O'Doherty, Tetrahedron Lett.
2004, 45, 1005-1009. 27.
"Facial Selectivity of the Sharpless Bromine Catalyzed Aziridination
Reaction." A. C. Schmitt, C. M. Smith, E. A. Voight and G. A. O’Doherty, Heterocycles,
2004, 62, 635-642. Special
issue in honor of Leo A. Paquette’s 70th B’day. 26.
"A
Palladium-Catalyzed Glycosylation Reaction: The de Novo Synthesis of Natural and
Unnatural Glycosides."
R. S.
Babu and G. A. O’Doherty,
J. Am. Chem. Soc. 2003,
125, 12406-12407. 25.
"Enantioselective Synthesis of Cryptocarya Triacetate, Cryptocaryolone and
Cryptocaryolone Diacetate." C. M. Smith and G. A. O'Doherty, Org.
Lett, 2003 5, 1959-1962. 24.
"An Enantioselective Synthesis of Phomopsolide B." J. M. Harris and G.
A. O'Doherty, Tetrahedron Lett. 2002, 43, 8195-8199. 23.
"Enantioselective Syntheses of Colletodiol, Colletol and Grahamimycin
A" T. J. Hunter and G. A. O’Doherty,
Org. Lett, 2002, 4, 4447-4450. 22.
"Enantioselective Synthesis of 2-Deoxy and 2,3-Dideoxy-hexoses" M. H.
Haukaas and G. A. O’Doherty,
Org. Lett. 2002, 4, 1771-1774. 21.
"An Enantioselective Synthesis of Tarchonanthuslactone" S. D. Garaas,
T. J. Hunter and G. A. O'Doherty, J. Org.
Chem. 2002, 67(8); 2682-2685. 20.
"Enantioselective Synthesis of N-Cbz-Protected
6-Amino-6-deoxy-Mannose, Gulose and Talose." M. H. Haukaas and G. A.
O’Doherty, Org. Lett. 2001,
3, 3899-3992. 19.
"An Enantioselective Synthesis of Cryptocarya Diacetate." T. J. Hunter
and G. A. O'Doherty, Org. Lett. 2001,
3, 2777-2780. 18.
"An Enantioselective Synthesis of Benzylidene Protected Syn-3,5-Dihydroxy
Carboxylate Esters via Osmium, Palladium, and Base Catalysis." T. J. Hunter
and G. A. O'Doherty, Org. Lett. 2001, 3, 1049-1052. 17.
"An Olefination Approach to the Enantioselective Syntheses of Several
Styryllactones" J. M. Harris and G. A. O'Doherty, Tetrahedron 2001, 57,
5161-5171. Special issue in honor of Barry M. Trost’s 60th Birthday. 16.
"Synthesis of D- and L-Deoxymannojirimycin via an Asymmetric
Aminohydroxylation of Vinylfuran." M. H. Haukaas and G. A. O'Doherty, Org.
Lett. 2001, 3, 401-404. 15.
"Enantioselective Synthesis of the Papulacandin Ring System: Conversion of
the Mannose Diastereoisomer into a Glucose Stereoisomer." D. Balachari and
G. A. O'Doherty, Org. Lett. 2000,
2, 4033-4036. 14.
"Enantioselective Syntheses of Isoaltholactone, 3-Epi-Altholactone and 5-Hydroxy Goniothalamin" J. M. Harris and
G. A. O'Doherty, Org. Lett. 2000,
2, 2983-2986. 13.
"A Rapid Enantioselective Assembly of a Manno-papulacandin Ring System via the Sharpless Catalytic
Asymmetric Dihydroxylation" D. Balachari, and G. A. O'Doherty, Org.
Lett. 2000, 2, 863-866. 12.
"Syntheses of Various D- and L-Hexoses via Diastereoselective and
Enantioselective Dihydroxylation Reactions." J. M. Harris, M. D. Keranen,
H. Nguyen, V. G. Young and G. A. O’Doherty, Carbohydr.
Res. 2000, 328(1), 17-36. Special
issue as part of the 1999, Carbohydrates
For The Next Millennium Symposium, South East Regional ACS Meeting. 11.
"Enantioselective Synthesis of 5-Substituted a,b-unsaturated
d-Lactones:
Application to the Synthesis of Styryllactones." J. M. Harris and G. A.
O’Doherty, Tetrahedron Lett. 2000,
41, 183-187. 10.
"Efficient Synthesis of 5-Aryl-2-vinylfurans by Palladium Catalyzed
Cross-Coupling Strategies." D. Balachari, L. Quinn and G. A. O'Doherty, Tetrahedron
Lett. 1999, 40, 4769-4773. 9.
"Asymmetric Aminohydroxylation of Vinylfuran." M. L. Bushey, M. H.
Haukaas G. A. O'Doherty J. Org. Chem. 1999,
64, 2984-2985. 8.
"Enantioselective Synthesis of Hexoses via the Sharpless Catalytic
Asymmetric Dihydroxylation Reaction of Vinylfuran." J. M. Harris, M. D.
Keranen and G. A. O'Doherty, J. Org. Chem.
1999, 64, 2982-2983. PUBLICATIONS:
before Minnesota 7.
"Asymmetric Synthesis of Allylic Sulfones. Useful Asymmetric Building
Blocks." B. M. Trost, M. G. Organ, G. A. O'Doherty, J. Am Chem. Soc. 1995, 117,
9662. 6.
"Consequences of Modulated Precompression Along Reaction Coordinates.
Synthesis, Crystallographic Structural Studies, and Rate of Intramolecular
Dyotropy in an Extended Series of Syn-Sesquinorbornene Disulfones." G. A.
O'Doherty, L. A. Paquette, R. D. Rogers J.
Am. Chem. Soc., 1994, 116,
10883. 5.
"Mechanistic Analysis of Double-Hydrogen Dyotropy in Syn-Sesquinorbornene
Disulfones. A Combined Kinetic and Theoretical Evaluation of Primary Deuterium
Isotope Effects." K. N. Houk, Y. Li, M. A. McAllister, G. A. O'Doherty, L.
A. Paquette, W. Siebrand, Z. K. Smedarchina, J. Am. Chem. Soc., 1994, 116,
10895. 4.
"Intramolecular Reaction Rate is Not Determined Exclusively by the Distance
Separating Reaction Centers. The Kinetic Consequences of Modulated Ground State
Strain on Dyotropic Hydrogen Migration in Systems of Very Similar Geometric
Disposition." L. A. Paquette, G. A. O'Doherty, R. D. Rogers, J.
Am. Chem. Soc., 1991, 113, 7761. 3.
"Structure Analysis of a Camphor Derived Cyclopentadienyl Lithium Compound
by NMR and MNDO. A Ternary Equilibrium in Tetrahydrofuran." W. Bauer, G. A.
O'Doherty, P. V. R. Schleyer, L. A. Paquette, J. Am. Chem. Soc., 1991, 113,
7093. 2.
"Stereoselective Access to the Three Diisodicyclopentadienyltitanium
Dichlorides." C. Sornay, P. Meunier, B. Gautheron, G. A. O'Doherty, L. A.
Paquette, Organometallics, 1991,
10, 2082. 1.
"Stereochemically Uniform Mode of Iron Carbonyl Complexation to Spirocyclic
Isodicyclopentadienes." L. A. Paquette, G. A. O'Doherty, B. L. Miller, R.
D. Rogers, A. L. Reingold and S. L. Geib, Organometallics,
1989, 8, 2167. REVIEWS and BOOK
CHAPTERS: 1. "Achmatowicz
Approach To 5,6-Dihydro-2H-Pyran-2-One
Containing Natural Products” in Strategy
and Tactics in Natural Product Synthesis, Michael Harmata Ed., by Joel
M. Harris, Miaosheng Li, Jana G. Scott and George A. O’Doherty,
ELSEVIER, London, 2004. 2. "Several Approaches to
Perhydrohistrionicotoxin: Setting an Azaspirocenters" Mortensen, M. S.; O’Doherty, G. A. ChemTracts-Organic
Chemistry 2004, 17, 261-268. 3. "Stereocontrolled Total Synthesis of
(+)-Streptazolin"
Zhou, M.; O’Doherty, G. A. ChemTracts-Organic
Chemistry 2004, 17,
593-599. 4. "Stereocontrolled Synthesis of the
Polyol Portion in Polyene Macrolide Natural Products" Dougherty, J.; Zhou, M.; O’Doherty, G. A. ChemTracts-Organic
Chemistry 2005, 18, 349-363. 5. "Recent Advances in 1,2-diamination
of Alkenes"
Mortensen, M. S.; O’Doherty, G. A. ChemTracts-Organic
Chemistry, ChemTracts-Organic
Chemistry 2005, 18,
555-561. 6. "Methallyl Bromide." (Update)
O’Doherty, G. A.; Gao, D. in Encyclopedia
of Reagents for Organic Synthesis, L. A. Paquette, Ed. John Wiley and Sons
LTD, England, 2006. 7. "Methallyl Chloride." (Update)
O’Doherty, G. A.; Gao, D. in Encyclopedia
of Reagents for Organic Synthesis, L. A. Paquette, Ed. John Wiley and Sons
LTD, England, 2006. 8. "De Novo Synthesis in Carbohydrate
Chemistry: From furans to
Monosaccharides and oligosaccharides."
in ACS Symposium Series 990, Chemical
Glycobiology, Xi Chen, Randall Halcomb and Peng George Wang Eds., by
Xiaomei Yu and George A. O’Doherty, ACS, Washington, 2008,
pp. 3-22. 9. "Cyclohexa-1,3-diene." O’Doherty, G. A.; Guppi, S. in Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed. John Wiley and Sons LTD, England, 2008. BOOK REVIEWS :
1.
Book
Review of: “Medicinal Chemistry of Bioactive Natural Products” Edited by
Xiao-Tian Liang and Wei-Shuo Fang (Chinese Academy of Medical Sciences, Beijing,
China). John Wiley & Sons, Inc.: Hoboken, NJ, 2006. xx + 460 pp. $89.95.
ISBN 0-471-66007-8. O'Doherty, G.
A. J. Am. Chem. Soc; 2006, 128,
12029-12029. 2. Book Review of: “Iminosugars: From Synthesis to
Therapeutic Applications”
Edited by Philippe
Compain and Olivier R. Martin (CNRS, University of Orleans, France): Chichester,
2007. xiv + 468 pp. $170.00. ISBN 978-0-470-03391-3. O'Doherty, G. A. J. Am.
Chem. Soc; 2008, 130,
6651-6651. PATENTS : 1. "Novel pyranose stereoisomers and methods for producing unnatural sugars via palladium catalyzed glycosylation” US Patent Application; US 20070254333 A1, 04/26/2007 George A. O’Doherty.
1.
National Organic Symposium, San Antonio, TX, June 3, 1997. 2.
Gordon Conference: Organic Reaction and Processes, Henniker, VT, August 2, 1997. 3.
National ACS Meeting, Dallas, TX, April 2, 1998. 4.
Great Lakes Regional ACS Meeting, Milwaukee, WI, June 3, 1998. 5.
Gordon Conference: Organic Reaction and Processes, Henniker, VT, August 2, 1998. 6.
National ACS Meeting, Boston, MA, August 27, 1998. |
