Horacio F Olivo

Horacio F Olivo

  • Associate Professor, Department of Pharmaceutical Sciences and Experimental Therapeutics / Division of Medicinal and Natural Products Chemistry

Office

S319 PHAR

Phone

(319) 335-8849

Research Narrative

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.

Curriculum vitae

Education
BS, Chemical Engineering, Universidad La Salle (ULSA)
MS, Organic Chemistry, Universidad Nacional Autonoma de Mexico (UNAM)
PhD, Synthetic Organic Chemistry, Virginia Polytechnic Institute and State University (Virginia Tech)

Professional Experience
1992-1993, Exeter University (UK), Postdoctoral Research Associate, laboratories of Stanley M. Roberts
1994-1995, The University of Virginia, Postdoctoral Research Associate, laboratories of Sidney M. Hecht
1995-2002, The University of Iowa, College of Pharmacy, Assistant Professor
2002-present, The University of Iowa, College of Pharmacy, Associate Professor

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
Lechuga-Eduardo, H., Olivo, H. F., Romero, M. Syntheses of 4-Substituted 2-(Trichloromethyl)quinazolines under Mild Conditions by Benzyne [4+2] Cycloaddition. Eur. J. Org. Chem. 2014; 27, 5910-5913.

Rios, M. Y., Olivo, H. F. Chapter 3 – Natural and Synthetic Alkamides: Applications in Pain Therapy. In Studies in Natural Products Chemistry; 2014; Vol. 43, pp. 79–121.

Rivas, V. M., Munive, L., Olivo, H. F. Thio-Michael-Aldol-Cyclization Cascade of N-Enoyl Thiazolidinethiones with Aliphatic Aldehydes and Cyclic Ketones. Synlett 2014; 25, 876-880.

Munive, L., Dzakuma, S. A., Olivo, H. F. Stereochemical Control on the Michael Addition of Chiral 1,3-Oxazolidine-2-thiones to N-Crotonyl 1,3-Oxazolidin-2-ones. Tetrahedron Lett. 2013; 54, 1230-1232.

Minor-Villar, L., Tello-Aburto, R., Olivo, H. F., Fuentes, A., Romero-Ortega, M. Desulfurization-Oxygenation of Chiral 1,3-Thiazolidine-2-thiones and 1,3-Oxazolidine-2-thiones Using Propylene Oxide and Microwave Irradiation. Synlett  2012; 23, 2835-2839.

Perez-Picaso, L., Olivo, H. F., Argotte-Ramos, R., Rios, M. Y. Linear and cyclic dipeptides with antimalarial activity. Bioorg. Med. Chem. Lett. 2012; 22, 7048-7051.

Munive, L., Rivas, V. M., Ortiz, A., Olivo, H. F. Oxazolidine-2-thiones and Thiazolidine-2-thiones as Nucleophiles in Intermolecular Michael Additions. Org. Lett. 2012; 14, 3514-3517.

Rodriguez-Cárdenas, E., Sabala, R., Romero-Ortega, M., Ortiz, A., Olivo, H.F. Chemoselective aromatic C-H insertion of α-diazo-β-ketoesters catalyzed by dirhodium(II) carboxylates. Org Lett. 2012;14(1):238-40. PubMed PMID: 22128849.

Sabala, R., Hernández-García, L., Ortiz, A., Romero, M., Olivo, H.F. Diastereoselective conjugate addition of organocuprates to chiral N-enoyl oxazolidinethiones. Org Lett. 2010;12(19):4268-70.PMID: 20806950

Liu, D., O'Leary, B., Iruthayanathan, M., Love-Homan, L., Perez-Hernandez, N., Olivo, H.F., Dillon, J.S. Evaluation of a novel photoactive and biotinylated dehydroepiandrosterone analog. Mol Cell Endocrinol. 2010;328(1-2):56-62. PubMed PMID: 20670672.

Olivo, H.F., Perez-Hernandez, N., Liu, D., Iruthayanathan, M., O'Leary, B., Homan, L.L., Dillon, J.S. Synthesis and application of a photoaffinity analog of dehydroepiandrosterone (DHEA). Bioorg Med Chem Lett. 2010;20(3):1153-5. PubMed PMID: 20031404; PubMed Central PMCID: PMC2818606.

Pérez-Picaso, L., Escalante, J., Olivo, H.F., Rios, M.Y. Efficient microwave assisted syntheses of 2,5-diketopiperazines in aqueous media. Molecules. 2009;14(8):2836-49. PubMed PMID: 19701127.

Osorio-Lozada, A., Olivo, H.F. Diastereoselective preparation of substituted delta-valerolactones. synthesis of (3R,4S)- and (3R,4R)-simplactones. J Org Chem. 2009;74(3):1360-3. PubMed PMID: 19102676.

Tello-Aburto, R., Olivo, H.F. A formal synthesis of the auriside aglycon. Org Lett. 2008 Jun 5;10(11):2191-4. Epub 2008 May 8. PubMed PMID: 18461949. Osorio-Lozada A, Olivo HF. Indene-based thiazolidinethione chiral auxiliary for propionate and acetate aldol additions. Org Lett. 2008;10(4):617-20. PubMed PMID: 18205374.

Olivo, H.F., Tovar-Miranda, R., Barragán, E. Synthesis of (-)-stemoamide using a stereoselective anti-aldol step. J Org Chem. 2006;71(8):3287-90. PubMed PMID: 16599632.

Barragán, E., Olivo, H.F., Romero-Ortega, M., Sarduy S. Stereoselective addition of the titanium enolate of N-acetyl (4S)-isopropyl-1,3-thiazolidine-2-thione to five-membered N-acyl iminium ions. J Org Chem. 2005;70(10):4214-7. PubMed PMID: 15876124.

Velázquez, F., Olivo, H.F. Synthesis of bicyclic gamma-ylidenetetronates. Org Lett. 2002;4(19):3175-8. PubMed PMID: 12227742.

Olivo, H.F., Hemenway, M.S. Total Synthesis of (+/-)-Epibatidine Using a Biocatalytic Approach. J Org Chem. 1999;64(24):8968-8969. PubMed PMID: 11674810.

Olivo, H.F., Colby, D.A., Hemenway, M.S. Syntheses of New Open-Ring and homo-Epibatidine Analogues from Tropinone. J Org Chem. 1999;64(13):4966-4968. PubMed PMID: 11674583.