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Horacio F. Olivo
Division of Medicinal and Natural Products Chemistry
College of Pharmacy, University of Iowa
115 S. Grand Ave.
Iowa City, IA 52242-1112
Tel: 319-335-8849
FAX: 319-335-8766
email: horacio-olivo@uiowa.edu
Education
- B.S., Chemical Engineering,
Universidad La Salle (ULSA),
- M.S., Organic Chemistry,
Universidad Nacional Autonoma de Mexico (UNAM),
- Ph.D., Synthetic Organic Chemistry,
Virginia Polytechnic Institute and State University (Virginia Tech)
For more information visit our Web-site:
Olivo Research Group
Olivo Research Presentation |
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| Professional Experience |
| Exeter University (UK), Postdoctoral Research Associate, laboratories of Stanley M. Roberts, 1992-1993 |
| The University of Virginia, Postdoctoral Research Associate, laboratories of Sidney M. Hecht, 1994-1995 |
| University of Iowa, College of Pharmacy, Assistant Professor, 1995-2002 |
| University of Iowa, College of Pharmacy, Associate Professor, 2002- |
| Research |
We have three main research program areas in our group. The first one is on the total syntheses of novel cytotoxic marine marcrolactones. We are currently focused on the syntheses of 14-membered ring callipeltosides and aurisides. A second theme is to develop chemical strategies for the syntheses of complex Stemona alkaloids. These molecules possess challenging structures and potent biological activity. The third area of research is the application of biotransformations to problems in synthetic organic chemistry. Research efforts include the preparation of chiral synthons by enzymatic desymmetrization of meso-compounds to single enantiomers and microbial hydroxylation of heteroatoms and unactivated carbons. These chiral synthons are then employed in the total enantioselective syntheses of natural products with great biological importance: marine glycosylated and halogenated macrolides and complex alkaloids of great biological significance. |
| Representative Publications |
Baeyer-Villiger Oxidation of Substituted Cyclohexanones via Lipase-mediated Perhydrolysis Utilizing Urea-Hydrogen Peroxide in Ethyl Acetate. Maria Yolanda Rios, Enrique Salazar, and Horacio F. Olivo. Green Chemistry 2007, in press. |
Lipase-mediated Epoxidation Utilizing Urea-Hydrogen Peroxide in Ethyl Acetate. Emmanuel G. Ankudey, Horacio F. Olivo, and Tonya L. Peeples. Green Chemistry 2006, 8, 923-926. |
Model Studies on the Ring Construction of the Auriside Macrolactone. Rodolfo Tello-Aburto, Adrian Ochoa-Teran, and Horacio F. Olivo. Tetrahedron Lett. 2006, 47, 5915-5917. |
Synthesis of (-)-Stemoamide Using a Stereoselective anti-Aldol Step. Horacio F. Olivo, Ricardo Tovar-Miranda and Efrain Barragan. J. Org. Chem. 2006, 71, 3287-3290. |
Microbial Oxidation/Amidation of Benzhydrylsulfanyl Acetic Acid. Synthesis of (+)-Modafinil. Horacio F. Olivo, Antonio Osorio-Lozada, and Tonya L. Peeples. Tetrahedron: Asymmetry 2005, 16, 3507
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| Stereoselective Addition of the Titanium Enolate of N-Acetyl (4S)-Isopropyl-1,3-thiazolidione-2-thione to 5-Membered N-Acyl Iminium Ions. Efrain Barragan, Horacio F. Olivo, Moises Romero-Ortega, and Seth Sarduy. J. Org. Chem. 2005, 70, 4214-4217. |
| Syntheses and Determination of the Absolute Stereochemistry of the Enantiomers of Adrafinil and Modafinil. Antonio Osorio-Lozada, Thomas Prisinzano and Horacio F. Olivo. Tetrahedron: Asymmetry 2004, 15, 3811-3815. |
| Stereoselective Aldol Additions of Titanium Enolates of N-Acetyl-4-Isopropyl-Thiazolidinethiones. Mathis B. Hodge and Horacio F. Olivo. Tetrahedron 2004, 60, 9397-9403. |
| The Meinwald Reaction of Alkyl Propionates. Synthesis of the C1-C9 Fragment of Aurisides. Maria-Yolanda Rios, Francisco Velazquez and Horacio F. Olivo. Tetrahedron 2003, 59, 6529-6536. |
| Microbial C-Hydroxylation and beta-4-O-Methylglucosidation of Methyl-Benzamide 7-Azanorbornane Ethers with Beauveria bassiana Horacio F. Olivo, Tonya L. Peeples, Maria-Yolanda Rios, Francisco Velázquez, Jin-Woo Kim and Someet Narang. Journal of Molecular Catalysis B: Enzymatic 2003, 21(3), 97-105. |
| Synthesis of Bicyclic gamma-Ylidenetetronates. Francisco Velázquez and Horacio F. Olivo. Organic Letters 2002, 4, 3175-3178. |
| Synthesis of the C10-C17 Fragment of Aurisides and Callipeltosides. Moises Romero-Ortega, David A. Colby and Horacio F. Olivo. Tetrahedron Lett. 2002, 43, 6439-6441. |
| The Application of Chiral Oxazolidinethiones and Thiazolidinethiones in Asymmetric Synthesis. Francisco Velázquez and Horacio F. Olivo. Current Organic Chemistry 2002, 6, 303-340. |
| Recent Syntheses of Epibatidine. A Review. Horacio F. Olivo and Michael S. Hemenway. Organic Preparations and Procedures International 2002, 34, 1-26. |
| Synthetic Studies on the trans-Chlorocyclopropane Dienyne Side Chain of Callipeltoside-A. Horacio F. Olivo, Francisco Velazquez and Henrique C. Trevisan. Organic Letters 2000, 2, 4055-4058. |
| Synthesis of the C1-C9 Fragment of Callipeltoside-A. Francisco Velazquez and Horacio F. Olivo. Organic Letters 2000, 2, 1931-1933. |
| Synthesis of (±)-Epibatidine Utilizing a Biocatalytic Approach. Horacio F. Olivo and Michael S. Hemenway. J. Org. Chem. 1999, 64, 8968. |
| Syntheses of New Phosphorous-Containing Azabicycloalkanes and their Microbial Hydroxylation Using Beauveria bassiana. Michael S. Hemenway and Horacio F. Olivo. J. Org. Chem. 1999, 64, 6312. |
| Syntheses of New Open-Ring and homo-Epibatidine Analogues from Tropinone. Horacio F. Olivo, David A. Colby and Michael S. Hemenway. J. Org. Chem. 1999, 64, 4966. |
Synthesis and Microbial Hydroxylation of Some Azabicycloalkanes. Horacio F. Olivo, Michael S. Hemenway, and Mikail H. Gezginci. Tetrahedron Lett. 1998, 39, 11, 1309. |
Practical enantiodivergent syntheses of both enantiomers of carbovir, 1592U89 and six-membered ring analogues. Horacio F. Olivo and Jiaxin Yu. J. Chem. Soc., Perkin Trans 1 1998, 391. |
| New Preparation of Activated 2-Vinylaziridines from 1,4-Aminoalcohols. Horacio F. Olivo, Michael S. Hemenway, Amy C. Hartwig, and Raymond Chan. Synlett 1998, 247. |
| Enantioselective Synthesis of 5'-homo-Carbocyclic Nucleosides. Horacio F. Olivo and Jiaxin Yu. Tetrahedron: Asymmetry 1997, 8, 3785. |
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