Division of Medicinal and Natural Products Chemistry
Department of Pharmaceutical Sciences and Experimental Therapeutics
College of Pharmacy, The University of Iowa
115 S. Grand Ave, S319 PHAR
Iowa City, IA 52242-1112
Tel: 319-335-8849
Fax: 319-335-8766
email: horacio-olivo@uiowa.edu
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
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 Jan 6;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 Oct 1;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 Oct 26;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 Feb 1;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 Jul 31;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 Feb 6;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 Feb 21;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 Apr 14;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 May 13;70(10):4214-7. PubMed PMID: 15876124.
Velázquez, F., Olivo, H.F. Synthesis of bicyclic gamma-ylidenetetronates. Org Lett. 2002 Sep 19;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 Nov 26;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 Jun 25;64(13):4966-4968. PubMed PMID: 11674583.