个人简介

Dr. Pettus worked as an undergraduate researcher in 1989 with Professor Tomás Hudlicky at VPI and subsequently obtained his Ph. D. degree in 1996 at the University of Rochester after working with Professor R. H. Schlessinger as a ACS organic graduate fellow. Following postgraduate work as an NSF Postdoctoral Fellow at Columbia University with Professor S. J. Danishefsky, Dr. Pettus joined the UCSB Chemistry Department in 1998. Dr. Pettus was awarded a Research Innovation Award from Research Corporation and in 2001 and NSF-Career Grant. His group currently has six graduate students and two postdocs.

研究领域

Organic & Bioorganic/Molecular Design & Synthesis/Biomedical Sciences/Biology-Inspired Chemistry & Physics

Our research program pursues new methods and strategies for constructing architecturally complex tetramic acid derivatives. Chiral tetramic acids and their derivatives are significant, because this structural motif is embedded in a multitude of natural products that display a dizzying array of biological activities. Their uses include potent antimicrobial therapies, as well as noteworthy applications as antiviral, and antifungal treatments. Several tetramic acids demonstrate insecticide and cytotoxic properties, as well as an ability to perturb quorum sensing and inhibit enzymes. Given their natural prevalence, biological importance, and apparent simplicity, it was surprising for us to learn that general synthetic methods leading to their enantioselective construction are lacking. Most synthetic chemists choose to build or buy the stereocenters, and then construct the fragile heterocyclic ring system of the chiral tetramic acid near then end of their effort. Our goal is to develop new strategies and methods to improve the efficiency for building current and ever more challenging architectures containing this heterocyclic motif. The total synthesis of the natural product tetrapetalone A presently serves as the backdrop and provides motivations for our future plans. Previous synthetic efforts aimed at the tetrapetalones, as well as current omissions in the chemical literature have identified and illuminated a clear need for the development of new methods to assemble this and complex chiral tetramic acid (TA) architectures in an enantioselective manner. We propose to examine a new vinylation reagent, along with three novel enantioselective methods aimed at C-C bond formation, as well as the enantioselective synthesis tetrapetalone-A itself to expand current chemic knowledge surrounding the tetramic acid motif. Undergraduate are expected to work for at least two summers and complete enough work for a publication. Contact Dr. Pettus if you are interested. Graduate students typically begin with a synthetic methods project before moving on to a natural product synthesis by their 2nd or 3rd year. Most graduate students finish their Ph.D. within five years earning 4-5 publications and finding employment in the pharmaceutical industry.

近期论文

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Feng, Z-G.; Bai, W. J.; Pettus, T. R. R.“Unified Total Syntheses of Medicarpin, Sophoracarpan A, and Kushecarpin A with Some Structural Revisions*” Angew. Chemie., 2014. ASAP, 69. Bai, W. J.; David, J. G.; Feng, Z-G.; Weaver, M. G.; Wu, K-L.; Pettus, T. R. R.“The Domestication of ortho-Quinone Methides” Acc. Chem. Res., 2014. ASAP, DOI: 10.1021/ar500330x 69. David, J. D.; Bai, W. J.; Weaver, M. G..; Pettus, T. R. R..“A General Diastereoselective Catalytic Vinylogous Aldol Reaction among Tetramic Acid-Derived Pyrroles” Org. Lett, 2014. 16, 4384-4387. PMID: 25119431 68. Weaver, M.G.; Bai, W. J.; Jackson, S.; Pettus, T. R. R..“Diels–Alder Construction of Regiodifferentiated meta-Amino Phenols and Derivatives” Org. Lett, 2014. 16, 1294-1297. PMID: 24524325 67. Weaver, M.G.; Pettus, T. R. R. “Synthesis of para- and ortho-Quinones” Comprehensive Organic Synthesis, 2nd ed Vol 7, Oxford: Elsevier; 2014. pp. 373-410. 66. Bai, W. J.; Jackson, S.; Pettus, T. R. R..“Mild Construction of 3-Methyl Tetramic Acids Enabling a Formal Synthesis of Palau’imide” Org. Lett, 2012, 14, 3862-3865. PMID: 22804621 65. Green, J. C.; Brown, E.; Pettus, T. R. R. ”Intramolecular Condensation via an ortho-Quinone Methide: Total Synthesis of (±)-Heliol” Org. Lett. 2012. 14, 2929 - 2931. PMID: 22650973. 64. Green, J. C.; Burnett, L.; Pettus, T. R. R..“Synthesis and Applications of Chroman Spiroketals” Pure Appl. Chem. 2012. 84, 1621-1631. 63. Cohn, E. P. M. T.; Wu, K-L.; Pettus, T. R. R. Reich, N. O. “A New Strategy for the Detection and Development of Tractable Telomerase Inhibitors” J. Med. Chem. 2012, 55, pp 3678–3686. PMID: 22413845. 62. Bai, W. J.; Green, J. C.; Pettus, T. R. R..“Total Syntheses of ent-Heliespirones A & C” J. Org. Chem. 2012, 77, 379-387. PMID: 22074003. 61. Green, J. C.; Alonso, S. J; Brown, E. R.; Pettus, T. R. R..“Total Synthesis and Repudiation of the Helianane Family” Org. Lett. 2011, 13, 5500–5503. PMID: 21928811. 60. Wu, K-L.; Mercado, E. V.; Pettus, T. R. R. “A Convergent Total Synthesis of (±)-γ-Rubromycin” J. Am. Chem. Soc. 2011, 133, 6114–6117. PMID: 21452818. 59. Jackson, S. K.; Wu, K-L; Pettus, T. R. R. Chapter 19 “Sequential Reactions Initiated by Oxidative Dearomatization. Biomimetic or Artifact?” in Biomimetic Organic Synthesis . 58. Cha, J. Y.; Burnett, L.; Davidson, J. B.; Pettus, T. R. R. “A Strategy for Late-Stage Divergent Syntheses of Scyphostatin Analogs” J. Org. Chem. 2011, 76, 1361–1371. PMID: 21250721. 57. Green, J.; Pettus, T. R. R. “An Oxidative Dearomatization Induced [5 + 2] Cascade Enabling the Efficient Syntheses of α-Cedrene, α-Pipitzol, and sec-Cedrenol” J. Am. Chem. Soc. 2011, 133, 1603–1608. PMID: 21194216. 56. Wenderski, T. A.; Marsini, M. A.; Pettus, T. R. R. “A Diastereoselective Formal Synthesis of Berkelic Acid” Org. Lett. 2011, 13, 118-121. PMID: 21138313. 55. Wenderski, T. A.; Hoarau, C; Mejorado, L.; Pettus, T. R. R. “Dearomatization Applications of I(III) Reagents and Unusual Reactivity Amongst Resorcinol Derived Cyclohexadienones” Tetrahedron, 2010, 66, 5873-5883. PMID: 23750053. 54. Cha, J. Y.; Huang, Y.; Pettus, T. R. R. “Total Synthesis of TK-57-164A, Isariotin F, and their Putative Progenitor Isariotin E” Angew. Chemie., Int. ed. 2009, 48, 9519-9521. PMID: 19921667 51. Wenderski, T. A.; DeNatale, V.; Pettus, T. R. R. “Synthesis of 2,2-disubstituted Pentalenes and Indenes by a Useful Modification to Nakamura’s DMCP [3 + 2] Cycloaddition Protocol ” Synlett, 2009, 2637-2641. PMID: 21442051. 50. Miller, L. A..; Marsini, M. A.; Pettus, T. R. R. “Chemoselective Reactions of 3-Benzyloxy-1,2-o-Quinone with Organometallic Reagents” Org. Lett. 2009, 11, 1955–1958. PMID: 19331343. 49.