F. Dean Toste

Last updated
Dean Toste
Born
Francisco Dean Toste

1971 (age 52–53)
Terceira, Azores, Portugal
Alma mater University of Toronto B.Sc. (1993) M.Sc. (1995)
Stanford University Ph.D. (2000)
Known for Organogold chemistry
asymmetric ion-pairing catalysis
Scientific career
FieldsChemistry
Institutions University of California, Berkeley
Thesis Part A. Phenols in palladium catalyzed reactions. Enantioselective total syntheses of (-)-galanthamine, (-)-aflatoxin B(1) and (-)-calanolide A and B. Part B. Ruthenium catalyzed carbon-carbon bond forming reactions  (2001)
Doctoral advisor Barry Trost
Other academic advisors Robert H. Grubbs
Ian Still
Website www.cchem.berkeley.edu/toste/index.html

F. Dean Toste (born 1971 in Terceira, Azores, Portugal) is the Gerald E. K. Branch Distinguished Professor of Chemistry at the University of California, Berkeley and faculty scientist at the chemical sciences division of Lawrence Berkeley National Lab. He is a prominent figure in the field of organic chemistry and is best known for his contributions to gold chemistry [1] and asymmetric ion-pairing catalysis. [2] Toste was elected a member of the National Academy of Sciences in 2020, [3] [4] and a member of the American Academy of Arts and Sciences in 2018. [5]

Contents

Education and training

Toste attended the University of Toronto for his undergraduate and masters studies in the group of Ian Still. [6] With Still, Toste developed several novel reactions of thiocyanates [7] [8] [9] [10] that were then applied towards the synthesis of the natural product Varacin. [11] He earned his B.Sc. in 1993 and his M.Sc. in 1995. Toste attended graduate school at Stanford University, earning his PhD under the supervision of Barry Trost in 2000 [12] While at Stanford, Toste published twenty-four publications on a range of topics, including phenols in palladium-catalyzed reactions, [13] [14] [15] and ruthenium-catalyzed carbon-carbon bond forming reactions. [16] [17] He also completed the enantioselective total syntheses of the natural products (−)-galanthamine, [18] (−)-aflatoxin B1 [19] [20] and (−)-calanolide A and B. [21]

From 2001 to 2002, Toste conducted postdoctoral studies at the California Institute of Technology with Robert H. Grubbs, where he worked on ruthenium-catalyzed cross-metathesis variants of the olefin metathesis reaction. [22] [23] [24]

Independent career

Toste joined the faculty at Berkeley in 2002 as an assistant professor. He was promoted to associate professor in 2006, and professor in 2009. In 2017, Toste was appointed the Gerald E. K. Branch Distinguished Professor. He has served as a faculty scientist at the chemical sciences division of Lawrence Berkeley National Lab since 2007. [25]

Awards and honors

Toste is the recipient of numerous awards for his work, including the Janssen Prize for Creativity in Organic Synthesis in 2018, [26] the Humboldt Research Award in 2016, [27] the Catalysis in Organic Chemistry Award from the Royal Society of Chemistry in 2018, and the American Chemical Society Cope Scholar and E. J. Corey Awards. [25]

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References

  1. ↑ Johansson, Magnus J.; Gorin, David J.; Staben, Steven T.; Toste, F. Dean (2005-12-01). "Gold(I)-Catalyzed Stereoselective Olefin Cyclopropanation". Journal of the American Chemical Society. 127 (51): 18002–18003. doi:10.1021/ja0552500. ISSN   0002-7863. PMID   16366541.
  2. ↑ Hamilton, Gregory L.; Kang, Eun Joo; Mba, Miriam; Toste, F. Dean (2007-07-27). "A Powerful Chiral Counterion Strategy for Asymmetric Transition Metal Catalysis". Science. 317 (5837): 496–499. Bibcode:2007Sci...317..496H. doi:10.1126/science.1145229. ISSN   0036-8075. PMID   17656720. S2CID   14368583.
  3. ↑ "2020 NAS Election".
  4. ↑ "F. Dean Toste". www.nasonline.org. Retrieved 2021-05-24.
  5. ↑ "F. Dean Toste". American Academy of Arts & Sciences. Retrieved 2021-05-24.
  6. ↑ Toste, Francisco Dinarco (1995). The total synthesis of varacin: novel applications of thiocyanate in organic synthesis (M.Sc. Thesis). University of Toronto. ISBN   0612075486.
  7. ↑ Toste, F. Dean; Stefano, Vittorio De; Still, Ian W. J. (2006-09-23). "A Versatile Procedure for the Preparation of Aryl Thiocyanates Using N-Thiocyanatosuccinimide (NTS)". Synthetic Communications. 25 (8): 1277–1286. doi:10.1080/00397919508012691.
  8. ↑ Toste, F.Dean; Laronde, Frank; Still, Ian W.J. (1995-04-24). "Thiocyanate as a versatile synthetic unit: Efficient conversion of ArSCN to aryl alkyl sulfides and aryl thioesters". Tetrahedron Letters. 36 (17): 2949–2952. doi:10.1016/0040-4039(95)00445-I. ISSN   0040-4039.
  9. ↑ Toste, F.Dean; Still, Ian W.J. (1995-06-19). "Preparation of t-butyl sulfides by a novel ligand-transfer reaction of aryl thiocyanates". Tetrahedron Letters. 36 (25): 4361–4364. doi:10.1016/0040-4039(95)00798-H. ISSN   0040-4039.
  10. ↑ Still, Ian W. J.; Toste, F. Dean (1996-01-01). "Reduction of Aryl Thiocyanates with SmI2 and Pd-Catalyzed Coupling with Aryl Halides as a Route to Mixed Aryl Sulfides". The Journal of Organic Chemistry. 61 (22): 7677–7680. doi:10.1021/jo961029h. ISSN   0022-3263. PMID   11667721.
  11. ↑ Toste, F. Dean; Still, Ian W. J. (1995). "A New Route to the Synthesis of the Naturally Occurring Benzopentathiepin Varacin". Journal of the American Chemical Society. 117 (27): 7261–7262. doi:10.1021/ja00132a033. ISSN   0002-7863.
  12. ↑ Toste, Francisco Dean (2001). Part A : phenols in palladium catalyzed reactions. Enantioselective total syntheses of (--)-galanthamine, (--)-aflatoxin B₁ and (--)-calanolide A and B. Part B : ruthenium catalyzed carbon-carbon bond forming reactions (3 vols., Ph.D. Thesis). Stanford University.
  13. ↑ Trost, Barry M.; Toste, F. Dean (1998). "Asymmetric O- and C-Alkylation of Phenols". Journal of the American Chemical Society. 120 (4): 815–816. doi:10.1021/ja972453i. ISSN   0002-7863.
  14. ↑ Trost, B. M.; Toste, F. D. (1999-04-30). "Regio- and Enantioselective Allylic Alkylation of an Unsymmetrical Substrate: A Working Model". Journal of the American Chemical Society. 121 (19): 4545–4554. doi:10.1021/ja9828713. ISSN   0002-7863.
  15. ↑ Trost, Barry M.; Toste, F. Dean; Greenman, Kevin (2003-03-20). "Atom Economy. Palladium-Catalyzed Formation of Coumarins by Addition of Phenols and Alkynoates via a Net C−H Insertion". Journal of the American Chemical Society. 125 (15): 4518–4526. doi:10.1021/ja0286573. ISSN   0002-7863. PMID   12683822.
  16. ↑ Trost, Barry M.; Toste, F. Dean (2000). "Ruthenium-Catalyzed Cycloisomerizations of 1,6- and 1,7-Enynes". Journal of the American Chemical Society. 122 (4): 714–715. doi:10.1021/ja993401r. ISSN   0002-7863.
  17. ↑ Trost, Barry M.; Toste, F. Dean; Shen, Hong (2000-02-25). "Ruthenium-Catalyzed Intramolecular [5 + 2] Cycloadditions". Journal of the American Chemical Society. 122 (10): 2379–2380. doi:10.1021/ja993400z. ISSN   0002-7863.
  18. ↑ Trost, Barry M.; Toste, F. Dean (2000-10-25). "Enantioselective Total Synthesis of (−)-Galanthamine". Journal of the American Chemical Society. 122 (45): 11262–11263. doi:10.1021/ja002231b. ISSN   0002-7863.
  19. ↑ Trost, Barry M.; Toste, F. Dean (1999-04-01). "Palladium-Catalyzed Kinetic and Dynamic Kinetic Asymmetric Transformation of 5-Acyloxy-2-(5H)-furanone. Enantioselective Synthesis of (−)-Aflatoxin B Lactone". Journal of the American Chemical Society. 121 (14): 3543–3544. doi:10.1021/ja9844229. ISSN   0002-7863.
  20. ↑ Trost, Barry M.; Toste, F. Dean (2003). "Palladium Catalyzed Kinetic and Dynamic Kinetic Asymmetric Transformations of γ-Acyloxybutenolides. Enantioselective Total Synthesis of (+)-Aflatoxin B1and B2a". Journal of the American Chemical Society. 125 (10): 3090–3100. doi:10.1021/ja020988s. ISSN   0002-7863. PMID   12617676.
  21. ↑ Trost, Barry M.; Toste, F. Dean (1998-09-01). "A Catalytic Enantioselective Approach to Chromans and Chromanols. A Total Synthesis of (−)-Calanolides A and B and the Vitamin E Nucleus". Journal of the American Chemical Society. 120 (35): 9074–9075. doi:10.1021/ja981142k. ISSN   0002-7863.
  22. ↑ Toste, F. Dean; Chatterjee, Arnab K.; Grubbs, Robert H. (2002-01-01). "Functional group diversity by ruthenium-catalyzed olefin cross-metathesis". Pure and Applied Chemistry (in German). 74 (1): 7–10. doi: 10.1351/pac200274010007 . ISSN   1365-3075. S2CID   96948773.
  23. ↑ Chatterjee, Arnab K.; Toste, F. Dean; Choi, Tae-Lim; Grubbs, Robert H. (2002). "Ruthenium-Catalyzed Olefin Cross Metathesis of Styrenes as an Alternative to the Heck and Cross-Coupling Reactions". Advanced Synthesis & Catalysis. 344 (6–7): 634–637. doi:10.1002/1615-4169(200208)344:6/7<634::AID-ADSC634>3.0.CO;2-K. ISSN   1615-4169.
  24. ↑ Chatterjee, A. K.; Toste, F. D.; Goldberg, S. D.; Grubbs, Robert H. (2003-01-01). "Synthesis of coumarins by ring-closing metathesis". Pure and Applied Chemistry (in German). 75 (4): 421–425. doi: 10.1351/pac200375040421 . ISSN   1365-3075. S2CID   98121109.
  25. 1 2 "Dean Toste CV (2020)" (PDF).
  26. ↑ "Janssen Prize for Creativity in Organic Synthesis - Prof. F. D. Toste". www.janssenpharmaceuticaprize.com. Retrieved 2021-05-24.
  27. ↑ "Professor Dean Toste recipient of prestigious Humboldt Research Award | College of Chemistry". chemistry.berkeley.edu. Retrieved 2021-05-24.
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