Publications

75. A Computational Framework to Explore Large-scale Biosynthetic Diversity, Navarro-Muñoz, J. C.; Selem-Mojica, N.; Mullowney, M. W.; Kautsar, S. A.; Tryon, J. H.; Parkinson, E. I.; De Los Santos, E. L. C.; Yeong, M.; Cruz-Morales, P.; Abubucker, S.; Roeters, A.; Lokhorst, W.; Fernadez-Guerra, A.; Teresa Dias Cappelini, T.; Goering, A. W.; Thomson, R. J.; Metcalf, W. W.; Kelleher, N. L.; Barona-Gomez, F.; Madema, M. H. Nat. Chem. Bio. 2019, Accepted.

74. Diene Synthesis by the Reductive Transposition of 1,2-Allenols, Rinaolo, V. J.; Robinson, E. R.; Diagne, A. B.; Schaus, S. E.; Thomson, R. J. Synlett 2019, Accepted.

73. Surface-Active β-Caryophyllene Oxidation Products at the Air/Aqueous Interface, Bé, A. G.; Liu, Y.; Tuladhar, A.; Bellcross, A. D.; Wang, Z.; Thomson, R. J.; Geiger, F. M. ACS Earth Space Chem. 2019, Accepted.

72. Synthesis and Surface Spectroscopy of α-Pinene Isotopologues and their Corresponding Secondary Organic Material, Upshur, M. A.; Vega, M. M.;  Bé, A. G.; H. M. Chase; Zhang, Y.; Tuladhar, A.; Chase, Z. A.; Fu, L.; Ebben, C. J.; Wang, Z.; Martin, S. T.; Geiger, F. M.; Thomson, R. J. Chem. Sci. 2019, Accepted.

71. Atmospheric β-Caryophyllene-Derived Ozonolysis Products at Interfaces, Bé, A. G.; H. M. Chase; Liu, Y.; Upshur, M. A.; Zhang, Y.; Tuladhar, A.; Chase, Z. A.; Bellcross, A. D.; Wang, H.-F.; Wang, Z.; Batista, V. S.; Martin, S. T.; Thomson, R. J.; Geiger, F. M. ACS Earth Space Chem. 2019, 3, 158–169.

70. Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space, Kearney, S. E. et. al. ACS Cent. Sci. 2018, 4, 1727–1741.

69. Observations of Sesquiterpenes and their Oxidation Products in Central Amazonia During the Wet and Dry Seasons, Yee, L.D.; Isaacman-VanWertz, G.; Wernis, R.A.; Meng, M.; Rivera, V.; Kreisberg, N. M.; Hering, S. V.; Bering, M. S.; Glasius, M.; Upshur, M. A.; Bé, A. G.; Thomson, R. J.; Geiger, F. M.; Offenberg, J. H.; Lewandowski, M.; Kourtchev, I.; Kalberer, M.; de Sá, S.; Martin, S. T.; Alexander, M. L.; Palm, B. B.; Hu, W.; Campuzano-Jost, P.; Day, D. A.; Jimenez, J. L.; Liu, Y.; McKinney, K. A.; Artaxo, P.; Viegas, J.; Manzi, A.; Oliveira, M. B.; de Souza, R.; Machado, L. A. T.; Longo, K.; Goldstein, A. H. Atmos. Chem. Phys. 2018, 18, 10433–10457.

68. Natural Products from Thioester Reductase Containing Biosynthetic Pathways, Mullowney, M. W.; McClure, R. A.; Robey, M. T.; Kelleher, N. L.; Thomson, R. J. Nat. Prod. Rep. 2018, 35, 847–878.

67. Total Synthesis of Tambromycin Enabled by Indole C–H Functionalization, Miley, G. P.; Rote, J. C.; Silverman, R. B.; Kelleher, N. L.; Thomson, R. J. Org. Lett. 2018, 20, 2369–2373.

66. Discovery of the Tyrobetaine Natural Products and Their Biosynthetic Gene Cluster via Metabologenomics, Parkinson, E. I.; Tryon, J. H.; Goering, A. W.; Ju, K-S.; McClure, R. A.; Kemball, J. D.; Zhukovsky, S.; Labeda, D. P.; Thomson, R. J.; Kelleher, N. L.; Metcalf, W. W. ACS Chem. Bio. 2018, 13, 1029–1037.

65. A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules, Robinson, E. R.; Thomson, R. J. J. Am. Chem. Soc. 2018, 140, 1956–1965.

64. Following Particle–Particle Mixing within Atmospheric Secondary Organic Aerosols Using Isotopically Labeled Terpenes, Ye, Q.; Upshur, M. A.; Robinson, E. S.; Geiger, F. M.; Sullivan, R. C.; Thomson, R. J.; Donahue, N. M. Chem. 2018, 4, 318–333.

63. Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transpositions of Allylic Diazenes, Jiang, Y.; Thomson, R. J., Schaus, S. E. Angew. Chem. Int. Ed. 2017, 56, 16631–16635.

62. Cloud Activation Potentials for Atmospheric α-Pinene and β-Caryophyllene Ozonolysis Products, Bé, A. G.; Upshur, M. A.; Liu, P.; Martin, S. T.; Geiger, F. M.; Thomson, R. J. ACS Cent. Sci. 2017, 3, 715–725.

61. The Effect of Hydroxyl Functional Groups and Molar Mass on the Viscosity of Non-Crystalline Organic and Organic-Water Particles, Grayson, J. W.; Song, M.; Evoy, E.; Upshur, M. A.; Ebrahimi, M.; Geiger, F. M.; Thomson, R. J.; Bertram, A. K. Atmos. Chem. Phys. 2017, 17, 8509–8524.

60. Highly Oxygenated Multifunctional Compounds in α‑Pinene Secondary Organic Aerosol, Zhang, X.; Lambe, A. T.; Upshur, M. A.; Brooks, W. A.; Bé, A. G.; Thomson, R. J.; Geiger, F. M.; Surratt, J. D.; Zhang, Z.; Gold, A.; Graf, S.; Cubison, M. J.; Groessl, M.; Jayne, J. T.; Worsnop, D. R.; Canagaratna, M. R. Env. Sci. Technol. 2017, 51, 5932–5940.

59. Unanticipated Stickiness of α-Pinene, Chase, H. M.; Ho, J.; Upshur, M. A.; Thomson, R. J.; Batista, V. S.; Geiger, F. M. J. Phys. Chem. A. 2017, 121, 3239–3246.

58. Enantioselective Synthesis of Allenes by Catalytic Traceless Petasis Reactions, Jiang, Y.; Diagne, A. B.; Thomson, R. J.; Schaus, S. E. J. Am. Chem. Soc. 2017, 139, 1998–2005.

tracelessallene

57. Orientations of Nonlocal Vibrational Modes from Combined Experimental and Theoretical Sum Frequency Spectroscopy, Chase, H. M.; Chen, S.; Fu, Li.; Upshur, M. A.; Rudshteyn, B.; Thomson, R. J.; Wang, H.-F.; Batista, V. S.; Geiger, F. M.. Chem. Phys. Lett. 2017, 683, 199–204.

nonlocal

56. Triflimide-Catalyzed Allylsilane Annulations of Benzylic Alcohols for the Divergent Synthesis of Indanes and Tetralins, Reddel, J. C. T.; Wang, W.; Koukounas, K.; Thomson, R. J.  Chem. Sci. 2017, 8, 2156–2160.

annulation

55. In Vitro Reconstruction of Nonribosomal Peptide Biosynthesis Directly from DNA Using Cell-Free Protein Synthesis, Goering, A. W.; Li, J.; McClure, R. A.; Thomson, R. J.; Jewett, M. C.; Kelleher, N. L. ACS Synth. Biol. 2017, 6, 39–44. [link]

CFPSyn

54. Elucidating the Rimosamide-Detoxin Natural Product Families and their Biosynthesis using Metabolite/Gene Cluster Correlations, McClure, R. A.; Goering, A. W.; Ju, K-S.; Baccile, J. A.; Schroeder, F. C.; Metcalf, W. W.; Thomson, R. J.; Kelleher, N. L. ACS Chem. Bio. 2016, 11, 3452–3460. [link]

Print

53. New Aspercryptins, Lipopeptides Natural Products Revealed by HDAC Inhibition in Aspergillus nidulans, Henke, M. T.; Soukup, A. A.; Goering, A. W.; McClure, R. A.; Thomson, R. J.; Keller, N. P.; Kelleher, N. L. ACS Chem. Bio. 2016, 11, 2117–2123. [link]

Aspercryptins

52. The Structural Elucidation, Chemical Synthesis and Biosynthesis of Prodiginine Alkaloids, Hu, D. X.; Withall, D. M.; Challis, G. L.; Thomson, R. J. Chem. Rev. 2016, 116, 7818–7853. [link]

ProdiginineCR

51. Sum Frequency Generation Spectroscopy and Molecular Dynamics Simulations Reveal A Rotationally Fluid Adsorption State of α-Pinene on Silica, Ho, J.; Psciuk, B. T.; Chase, H. M.; Rudshteyn, B.; Upshur, M. A.; Fu, L.; Thomson, R. J.; Geiger, F. M.; Batista, V. S. J. Phys. Chem. C. 2016, 120, 12578–12589. [link]

PineneSilica

50. Vibrational Mode Assignment of α-Pinene by Isotope Editing: One Down, Seventy-One to Go, Upshur, M. A.; Chase, H. M.; Strick, B. F.; Ebben, C. J.; Fu, L.; Wang, H.; Thomson, R. J.; Geiger, F. M. J. Phys. Chem. A. 2016, 120, 2684–2690. [link]

TOC

49. Metabologenomics: Correlation of Microbial Gene Clusters with Metabolites Drives Discovery of a Nonribosomal Peptide with an Unusual Amino Acid Monomer, Goering, A. W.; McClure, R. A.; Doroghazi, J. R.; Albright, J. C.; Haverland, N. A.; Zhang, Y.; Ju, K-S.; Thomson, R. J.; Metcalf, W. W.; Kelleher, N.L. ACS Cent. Sci. 2016, 2, 99–108. [link]

Tambro

48. Assessment of DFT for Computing Sum Frequency Generation Spectra of an Epoxydiol and a Deuterated Isotopologue at Fused Silica/Vapor Interfaces, Chase, H. M.; Rudshteyn, B.; Psciuk, B. T.; Upshur, M. A.; Strick, B. F.; Thomson, R. J.; Batista, V. S.; Geiger, F. M. J. Phys. Chem. B 2015, 120, 1919–1927. [link]

DFTepoxydiol

47. SAMDI Mass Spectrometry-Enabled High-Throughput Optimization of a Traceless Petasis Reaction, Diagne, A. B.; Li, S; Perkowski, G. A.; Mrksich, M.; Thomson, R. J. ACS Combi. Sci. 2015, 11, 658–662. [link]

SAMDI-allene

46. Total Synthesis of the Galbulimima Alkaloids Himandravine and GB17 using Biomimetic Diels–Alder Reactions of Double Diene Precursors, Larson, R. T.; Pemberton, R. P.; Franke, J. M.; Tantillo, D. J.; Thomson, R. J. J. Am. Chem. Soc. 2015, 137, 11197–11204. [link]

GB17-DA

45. Investigations into Apopinene as a Biorenewable Monomer for Ring-Opening Metathesis Polymerization, Strick, B. J.; Delferro, M.; Geiger, F. M.; Thomson, R. J. ACS Sustainable Chem. Eng. 2015, 3, 1278–1281. [link]

ROMP

44. Large-Scale Metabolomics Reveals a Complex Response of Aspergillus nidulans to Epigenetic Perturbation, Albright, J. C.; Henke, M. T.; Soukup, A. A.; McClure, R. A.; Thomson, R. J.; Keller, N. P.; Kelleher, N. K. ACS Chem. Biol. 2015, 10, 1535–1541. [link]

Omics

43. Beyond Local Group Modes in Vibrational Sum Frequency Generation, Chase, H. M.; Psciuk, B. T.; Strick, B. F.; Thomson, R. J.; Batista, V. S.; Geiger, F. M. J. Phys. Chem. A. 2015, 119, 3407–3414. [link]

IEPOX-modes

42. Accurate Lineshapes from Sub-1 cm-1 Resolution Sum Frequency Generation Vibrational Spectroscopy of α-Pinene at Room Temperature, Mifflin, A L.; Velarde, L.; Ho, J.; Psciuk, B. T.; Negre, C. F. A.; Ebben, C. J.; Upshur, M. A.; Lu, Z.; Strick, B. F.; Thomson, R. J.; Batista, V. S.; Wang, H.-F.; Geiger, F. M. J. Phys. Chem. A. 2015, 119, 1292–1302. [link]

Lineshapes

41. On Surface Order and Disorder of α-Pinene-Derived Secondary Organic Material, Shrestha, M.; Zhang, Y.; Upshur, M. A.; Liu, P.; Blair, S. L.; Wang, H.-F.; Nizkorodov, S. A.; Thomson, R. J.; Martin, S. T.; Geiger, F. M. J. Phys. Chem. A. 2015, 119, 4609–4617. (Special Issue in Honor of Prof. Mario Molina) [link]

RH-JPC

40. Enantioselective Synthesis of Metacycloprodigiosin via the “Wasserman Pyrrole”, Vega, M. M; Crain, D. M.; Konkol, L. C.; Thomson, R. J. Tetrahedron Lett. 2015, 56, 3228–3230. (Special Symposium in Print in Memory of Prof. Harry Wasserman) [link]

MCP-TL

39. Uptake of Epoxydiol Isomers Accounts for Half of the Particle-Phase Material Produced from Isoprene Photooxidation via the HO2 pathway, Liu, Y.; Kuwata, M.; Strick, B. F.; Geiger, F. M.; Thomson, R. J.; McKinney, K. A.; Martin, S. T. Env. Sci. Technol. 2015, 49, 250–258. [link]

IEPOX Uptake

38. Enantioselective Total Synthesis of (–)-Maoecrystal V, Zheng, C.; Dubovyk, I.; Lazarski, K. E.; Thomson, R. J. J. Am. Chem. Soc. 2014, 136, 17750–17756. [link]

MaoV-JACS

37. Climate-Relevant Physical Properties of Molecular Constituents for Isoprene-Derived Secondary Organic Aerosol Material, Upshur, M. A.;Strick, B. F.; McNeil, V. F.; Thomson, R. J.; Geiger, F. M. Atmos. Chem. Phys. 2014, 14, 10731–10740. [link]

IEPOXST

36. Recent Efforts in the Total Synthesis of Isodon Diterpenes, Lazarski, K. E.; Moritz, B. J.; Thomson, R. J. Angew. Chem. Int. Ed. 2014, 53, 10588–10599. [link]

IsodonReview

35. Total Synthesis of Propolisbenzofuran B, Jones, B. T; Avetta, C. T.; Thomson, R. J. Chem. Sci. 2014, 5, 1794–1798. [link]

Propolis

34. Towards the Identification of Molecular Constituents Associated with the Surfaces of Isoprene-derived Secondary Organic Aerosol (SOA) Particles, Ebben, C. J.; Strick, B. F.;Upshur, M. A.; Chase, H. M.; Achtyl, J. L.; Thomson, R. J.; Geiger, F. M. Atmos. Chem. Phys. 2014, 14, 2303–2314. [link]

IsopreneSFG

33. Total Synthesis of the Isodon Diterpene Sculponeatin N, Moritz, B. J.; Mack, D. J.; Tong, L.; Thomson, R. J. Angew. Chem. Int. Ed. 2014, 53, 2988–2991. [link]

32. Stereocontrolled Syntheses of Tetralone and Naphthyl-type Lignans by a One-Pot Oxidative [3,3] Rearrangement/Friedel–Crafts Arylation, Reddel, J. C. T.; Lutz, K. E.; Diagne, A. B.; Thomson, R. J. Angew. Chem. Int. Ed. 2014, 53, 1395–1398. [link]

31. Elimination of Butylcycloheptylprodigiosin as a Known Natural Product Inspired by an Evolutionary Hypothesis for Cyclic Prodigiosin Biosynthesis, Jones, B. T.; Hu, D. X.; Savoie, B. M; Thomson, R. J. J. Nat. Prod. 2013, 76, 1937–1945. [link]

30. Mechanism of Triflimide-Catalyzed [3,3]-Sigmatropic Rearrangements of N-Allylhydrazones—Predictions and Experimental Validation, Gutierrez, O; Strick, B. F.; Thomson, R. J.; Tantillo, D. J. Chem. Sci. 2013, 4, 3997–4003. [link]

29. Proteomics Guided Discovery of Flavopeptins: Anti-Proliferative Aldehydes Synthesized by a Reductase Domain-Containing Nonribosomal Peptide Synthetase , Chen. Y.; McClure, R. A.; Zheng, Y.; Thomson, R. J.; Kelleher, N. L. J. Am. Chem. Soc. 2013, 135, 10449–10456. [link]

28. Evaluation of ‘East-to-West’ Ether-Forming Strategies for the Total Synthesis of Maoecrystal V, Lazarski, K. E.; Akpinar, B.; Thomson, R. J. Tetrahedron Lett. 201354, 635-637. [link]

27. Gobichelin A and B: Mixed-Ligand Siderophores Discovered Using Proteomics, Chen, Y.; Unger, M.; Ntai, I.; McClure, R. A.; Albright, J. C.; Thomson, R. J.; Kelleher, N. L. Med. Chem. Commun. 20134, 233-238. [link]

26. Oxidative Coupling of Enolates, Enol Silanes, and Enamines: Methods and Natural Product Synthesis, Guo, F.; Clift, M. D.; Thomson, R. J. Eur. J. Org. Chem. 201226, 4881–4896[link]

25. Organic Constituents on the Surfaces of Aerosol Particles from Southern Finland, Amazonia, and California Studied by Vibrational Sum Frequency Generation, Ebben, C. J.; Shrestha, M.; Martinez, I. S.;  Corrigan, A. L.; Frossard, A. A.; Song, W. W.; Worton, D. R.; Petäjä, T.; Williams, J.; Russell, L. M.; Kulmala, M.; Goldstein, A. H.; Artaxo, P.; Martin, S. T.; Thomson, R. J.; Geiger, F. M. J. Phys. Chem. A2012,116, 8271–8290. [link]

24. Mundal, D. A.; Lutz, K. E.; Thomson, R. J. “A Direct Synthesis of Allenes by a Traceless Petasis Reaction,” J. Am. Chem. Soc2012134, 5782–5785. [link]

23. Larson, R. T.; Clift, M. D.; Thomson, R. J. “Total Synthesis of the Galbulimima Alkaloid (–)-GB17,” Angew. Chem. Int. Ed201251, 2481–2484. [link]

22. Konkol, L. C.; Guo, F.; Sarjeant, A. A.; Thomson, R. J. “Enantioselective Total Synthesis and Studies into the Configurational Stability of Bismurrayaquinone A,” Angew. Chem. Int. Ed. 2011, 50, 9931–9934. [link]

21. Strick, B. F.; Mundal, D. A.; Thomson, R. J. “An Oxidative [2,3]-Sigmatropic Rearrangement of Allylic Hydrazides,” J. Am. Chem. Soc.2011133, 14252–14255. [link]

20. Lutz, K. E.; Thomson, R. J. “A Hypervalent Iodide-Initiated Fragment Coupling Cascade of N-Allylhydrazones,” Angew. Chem. Int. Ed. 201150, 4437–4440. [link]

19. Hu, D. X.; Clift, M. D.; Lazarski, K. E.; Thomson, R. J. “Enantioselective Total Synthesis and Confirmation of the Absolute Stereochemistry and Relative Stereochemistry of Streptorubin B,” J. Am. Chem. Soc. 2011133, 1799–1804. [link]

18. Guo, F.; Konkol, L. C.; Thomson, R. J. “Enantioselective Synthesis of Biphenols from 1,4-Diketones by Traceless Central-to-Axial Chirality Exchange,“ J. Am. Chem. Soc. 2011,133, 18–20. [link]

 

17. Lazarski, K. E.; Hu, D. X.; Stern, C. L.; Thomson, R. J. “A Synthesis of the Carbocyclic Core of Maoecrystal V,” Org. Lett. 201012, 3010­–3013[link]

16. Mundal, D. A.; Avetta, Jr. C. T.; Thomson, R. J. “Triflimide Catalyzed Sigmatropic Rearrangement of N-Allylhydrazones as an Example of a Traceless Bond Construction,” Nature Chem. 20102, 294–297. [link]

15. Konkol, L. C.; Jones, B. T.; Thomson, R. J. “Oxidative Carbon–Carbon Bond Formation via Allyldimethylsilyl Enol Ethers,” Org. Lett. 200911, 5550–5553. [link]

14. Clift, M. D.; Thomson, R. J. “Development of a Merged Conjugate Addition/Oxidative Coupling Sequence. Application to the Enantioselective Total Synthesis of Metacycloprodigiosin and Prodigiosin R1,” J. Am. Chem. Soc. 2009131, 14579–14583. [link]

13. Mundal, D. A.; Lutz, K. E.; Thomson, R. J. “Stereoselective Diene Synthesis from N-Allylhydrazones,” Org.  Lett. 200911, 465–468. [link]

12. Avetta, Jr. C. T.; Konkol, L. C.; Taylor, C. N.; Dugan, K. C.; Stern, C. A.; Thomson, R. J. “Diastereoselective Oxidative Carbon–Carbon Bond Formation via Silyl Bis-enol Ethers,” Org. Lett. 20089, 5621–5624. [link]

11. Mundal, D. A.; Lee, J. J.; Thomson, R. J. “Tandem Carbon-Carbon and Carbon-Chlorine Bond Formation by Cu(II) Chloride-Promoted [3,3] Sigmatropic Rearrangement of N-Allylhydrazones,” J. Am. Chem. Soc. 2008130, 1148–1149. [link]

10. Clift, M. D.; Taylor, C. N.; Thomson, R. J. “Oxidative Carbon-Carbon Bond Formation via Silyl Bis-enol Ethers: Controlled Cross-coupling for the Synthesis of Quaternary Centers,” Org. Lett. 20079, 4667–4669. [link]

9. Kim, J.; Thomson, R. J. “Enantioselective Total Synthesis of the Osteoclastogenesis Inhibitor (+)-Symbioimine,” Angew. Chem. Int. Ed. 200746, 3104–3106. [link]

8. Thomson, R. J. “(S)-4-(Phenylmethyl)-2-thiazolidinethione,” In The Electronic Encyclopedia of Reagents for Organic Synthesis, Wiley, 2007. [link]
7. Morrison, E.; Chandler, P. M.; Thomson, R. J.; Mander, L. N. “Synthesis and Bioactivity of the Gibberellin, 18-Hydroxy-GA1 (GA132),” Org. Biomol. Chem., 2008, 6, 1416–1424. [link]
6. Crow, J. R.; Thomson, R. J.; Mander, L. N. “Synthesis and Confirmation of Structure for the Gibberellin GA131 (18-hydroxy-GA4),” Org. Biomol. Chem., 2006, 4, 2532–2544. [link]
5. Evans, D. A.; Thomson, R. J.; Franco, F. “Ni(II) Tol-BINAP-Catalyzed Enantioselective Michael Additions of b-Ketoesters and Unsaturated N-Acylthiazolidinethiones,” J. Am. Chem. Soc. 2005, 127, 10816–10817. [link]
4. Evans, D. A.; Thomson, R. J. “Ni(II) Tol-BINAP-Catalyzed Enantioselective Orthoester Alkylations of N-Acylthiazolidinethiones,” J. Am. Chem. Soc. 2005, 127, 10474–10475. [link]
3. Mander, L. N.; Thomson, R. J. “Total Synthesis of Sordaricin,” J. Org. Chem. 2005, 70, 1654–1670. [link]
2. Mander, L. N.; Thomson, R. J. “Total Synthesis of Sordaricin,” Org. Lett. 2003, 5, 1321­–1324. [link]
1. Mander, L. N.; Thomson, R. J. “C18-Hydroxylation of Gibberellins,” J. Chem. Soc., Perkin Trans. 1, 2000, 2893­–2894. [link]