F. Dean Toste Explained

Dean Toste
Birth Name:Francisco Dean Toste
Birth Place:Terceira, Azores, Portugal
Fields:Chemistry
Workplaces:University of California, Berkeley
Thesis Title: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
Thesis Url:https://www.proquest.com/pqdtglobal/docview/250190558/95F71B88DCED4282PQ
Thesis Year:2001
Doctoral Advisor:Barry Trost
Academic Advisors:Robert H. Grubbs
Ian Still
Known For:Organogold chemistry
asymmetric ion-pairing catalysis
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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]

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.

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. 10.1021/ja0552500. 16366541. 0002-7863.
  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. en. 317. 5837. 496–499. 10.1126/science.1145229. 0036-8075. 17656720. 2007Sci...317..496H. 14368583.
  3. Web site: 2020 NAS Election.
  4. Web site: F. Dean Toste. 2021-05-24. www.nasonline.org.
  5. Web site: F. Dean Toste. 2021-05-24. American Academy of Arts & Sciences. en.
  6. Book: Toste, Francisco Dinarco. The total synthesis of varacin: novel applications of thiocyanate in organic synthesis (M.Sc. Thesis). University of Toronto. 1995. 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. en. 10.1080/00397919508012691.
  8. 1995-04-24. Thiocyanate as a versatile synthetic unit: Efficient conversion of ArSCN to aryl alkyl sulfides and aryl thioesters. Tetrahedron Letters. en. 36. 17. 2949–2952. 10.1016/0040-4039(95)00445-I. 0040-4039. Toste. F.Dean. Laronde. Frank. Still. Ian W.J..
  9. 1995-06-19. Preparation of t-butyl sulfides by a novel ligand-transfer reaction of aryl thiocyanates. Tetrahedron Letters. en. 36. 25. 4361–4364. 10.1016/0040-4039(95)00798-H. 0040-4039. Toste. F.Dean. Still. Ian W.J..
  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. 10.1021/jo961029h. 11667721. 0022-3263.
  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. 10.1021/ja00132a033. 0002-7863.
  12. Book: Toste, Francisco Dean. 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. 2001.
  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. 10.1021/ja972453i. 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. 10.1021/ja9828713. 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. 10.1021/ja0286573. 12683822. 0002-7863.
  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. 10.1021/ja993401r. 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. 10.1021/ja993400z. 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. 10.1021/ja002231b. 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. 10.1021/ja9844229. 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. 10.1021/ja020988s. 12617676. 0002-7863.
  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. 10.1021/ja981142k. 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. de. 74. 1. 7–10. 10.1351/pac200274010007. 96948773. 1365-3075. free.
  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. en. 344. 6–7. 634–637. 10.1002/1615-4169(200208)344:6/7<634::AID-ADSC634>3.0.CO;2-K. 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. de. 75. 4. 421–425. 10.1351/pac200375040421. 98121109. 1365-3075. free.
  25. Web site: Dean Toste CV (2020).
  26. Web site: Janssen Prize for Creativity in Organic Synthesis - Prof. F. D. Toste. 2021-05-24. www.janssenpharmaceuticaprize.com. en.
  27. Web site: Professor Dean Toste recipient of prestigious Humboldt Research Award College of Chemistry. 2021-05-24. chemistry.berkeley.edu.

External links

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