Sarah E. Reisman Explained

Sarah E. Reisman
Fields:Chemistry
Organic Chemistry
Natural product
Workplaces:California Institute of Technology
Harvard University
Alma Mater:Connecticut College (BA)
Yale University (PhD)
Thesis Title:Total synthesis of (+/-) Welwitindolinone A isonitrile
Thesis Url:https://search.proquest.com/docview/304982298
Thesis Year:2006
Doctoral Advisor:John L. Wood
Academic Advisors:Eric Jacobsen

Sarah Elizabeth Reisman is the Bren Professor of Chemistry and the Chair of Division of Chemistry and Chemical Engineering at California Institute of Technology.[1] She received the (2013) Arthur C. Cope Scholar Award[2] and the (2014)[3] Tetrahedron Young Investigator Award for Organic Synthesis.[4] Her research focuses on the total synthesis of complex natural products and data-driven developments of asymmetric catalysis.

Early career and education

Undergraduate Studies

Reisman received a B.A. in chemistry from Connecticut College in 2001,[5] conducting research in the lab of Prof. Timo V. Ovaska[6] on the synthesis of tetracyclic terpenoid natural products, including phorbol.[7] [8]

Graduate Studies

Reisman obtained her Ph.D. from Yale University[9] in 2006, working with John L. Wood on the total synthesis of (±)-welwitindolinone A isonitrile.[10] Reisman's work included methodological developments towards a generalized skeleton, using nitrone cyclization and oxindole formation as linchpin transforms.[11]

Postdoctoral Studies

Reisman was an NIH Postdoctoral Fellow in the lab of Eric N. Jacobsen at Harvard University and worked with then-graduate student Abigail Doyle to develop an enantioselective substitution of silyl ketenes onto an alkoxy chloride via an oxocarbenium ion using a novel thiourea organocatalyst.[12]

Research

Reisman began her independent career as an assistant professor at Caltech in 2008[13] and was promoted to full professor in 2014.[14]

The Reisman lab focuses on the synthesis of complex natural products and development of new chemical reactions, and the interplay between those two fields.

The group completed the first enantioselective total syntheses of (–)-acetylaranotin (40 years after its isolation),[15] [16] (–)-maoecrystal Z,[17] (–)-8-demethoxyrunanine, and (–)-cepharatines A, C and D.[18] Their total synthesis of (+)-ryanodol was completed in 15 synthetic steps,[19] a significant improvement on the previous shortest synthetic route of 35 steps developed by Masayuki Inoue of the University of Tokyo.[20] [21] In 2019, Reisman and coworkers published the first total synthesis of isoryanoid diterpene (+)-perseanol in Nature.[22] Other completed total syntheses include natural products (+)-naseseazines A and B,[23] (+)-salvileucalin B,[24] (+)-psiguadial B[25] [26] [27] and (+)-pleuromutilin.[28]

The group's reaction methodology work has focused primarily on nickel catalysis,[29] cycloadditions,[30] and opening of strained-ring precursors.

Selected Awards and Honors

Reisman was awarded the Boehringer Ingelheim New Faculty Grant,[44] the Alfred P Sloan Foundation Fellowship[45] and a 5-year NSF CAREER Award in 2011.[46]

Notes and References

  1. Web site: Sarah E. Reisman Division of Chemistry and Chemical Engineering. 2021-04-28. cce.caltech.edu.
  2. Web site: Necessity is the Mother of Invention: Natural Products and the Chemistry They Inspire. www.chem.purdue.edu.
  3. Book: Tetrahedron.
  4. Web site: The Reisman Group. reismangroup.caltech.edu. en. 2018-07-26.
  5. Web site: Student Hosted Colloquia: Professor Sarah Reisman, Caltech Department of Chemistry. 2021-04-28. chemistry.stanford.edu.
  6. Web site: sarah reisman, Timo V. Ovaska – Google Search. 2021-04-28. www.google.com.
  7. Web site: Ovaska Research Group. Connecticut College. en. 2018-07-26.
  8. 2015-09-23. Bright Young Minds: Meet 10 scientists who are making their mark. Science News. en. 188. 7. 20–26. 10.1002/scin.2015.188007018. 0036-8423.
  9. Web site: Trager2020-04-29T14:00:00+01:00. Rebecca. Chemists amid coronavirus: Sarah Reisman. 2021-04-28. Chemistry World. en.
  10. Reisman. Sarah E.. Ready. Joseph M.. Weiss. Matthew M.. Hasuoka. Atsushi. Hirata. Makoto. Tamaki. Kazuhiko. Ovaska. Timo V.. Smith. Catherine J.. Wood. John L.. February 2008. Evolution of a Synthetic Strategy: Total Synthesis of (±)-Welwitindolinone A Isonitrile. Journal of the American Chemical Society. en. 130. 6. 2087–2100. 10.1021/ja076663z. 18198870. 0002-7863.
  11. Web site: Total Synthesis of -Welwitindolinone A Isonitrile. J.A.C.S. Communications.
  12. Reisman. Sarah E.. Doyle. Abigail G.. Jacobsen. Eric N.. June 2008. Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions. Journal of the American Chemical Society. EN. 130. 23. 7198–7199. 10.1021/ja801514m. 0002-7863. 2574628. 18479086.
  13. Web site: Caltech Faculty Receive Named Professorships. 2021-04-28. Division of Chemistry and Chemical Engineering. 9 October 2020 . en.
  14. Web site: Organic chemistry colloquium. 2021-04-28. UDaily.
  15. Codelli. Julian A.. Puchlopek. Angela L. A.. Reisman. Sarah E.. 2011-10-28. Enantioselective Total Synthesis of (−)-Acetylaranotin, a Dihydrooxepine Epidithiodiketopiperazine. Journal of the American Chemical Society. EN. 134. 4. 1930–1933. 10.1021/ja209354e. 0002-7863. 3271125. 22023250.
  16. Web site: Alkaloid Acetylaranotin Made After 40-Year Quest Chemical & Engineering News. Drahl. Carmen. cen.acs.org. 2018-07-29.
  17. Cha. J. Y.. Yeoman. J. T. S.. Reisman. S. E.. 2011-11-18. Synthesis of (-)-Maoecrystal Z. Synfacts. en. 2011. 12. 14964–7. 10.1055/s-0031-1289337. 21877709. 1861-1958.
  18. Ley. Steven V.. Frost. James R.. 2011-12-19. Synthesis of (–)-8-Demethoxyrunanine and (–)-Cepharatines A, C and D. Synfacts. en. 8. 1. 0014. 10.1055/s-0031-1289924. 100429449 . 1861-1958.
  19. Chuang. Kangway V.. Xu. Chen. Reisman. Sarah E.. 2016-08-26. A 15-step synthesis of (+)-ryanodol. Science. en. 353. 6302. 912–915. 10.1126/science.aag1028. 0036-8075. 5505075. 27563092. 2016Sci...353..912C.
  20. News: A Simpler Way To Make A Complicated Molecule. Lemonick. Sam. Forbes. 2018-07-26. en.
  21. Book: Pei-Qiang., Huang. Efficiency in natural products total synthesis. 2016. John Wiley & Sons. 9781118940204. [Place of publication not identified]. 132. 1046102804.
  22. Han. Arthur. Tao. Yujia. Reisman. Sarah E.. September 2019. A 16-step synthesis of the isoryanodane diterpene (+)-perseanol. Nature. en. 573. 7775. 563–567. 10.1038/s41586-019-1580-x. 31554978. 1476-4687. 2019Natur.573..563H. 7123484.
  23. Kieffer. Madeleine E.. Chuang. Kangway V.. Reisman. Sarah E.. 2013-04-03. Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B. Journal of the American Chemical Society. EN. 135. 15. 5557–5560. 10.1021/ja4023557. 0002-7863. 3662218. 23540731.
  24. Levin. S.. Nani. R. R.. Reisman. S. E.. 2011-05-19. Enantioselective Synthesis of (+)-Salvileucalin B. Journal of the American Chemical Society. en. 133. 4. 774–6. 10.1021/ja110192b . 21174417.
  25. Chapman. Lauren M.. Beck. Jordan C.. Wu. Linglin. Reisman. Sarah E.. 2016-08-02. Enantioselective Total Synthesis of (+)-Psiguadial B. Journal of the American Chemical Society. EN. 138. 31. 9803–9806. 10.1021/jacs.6b07229. 27452034. 0002-7863.
  26. Web site: An enantioselective synthesis of (+)-psiguadial B Chemical & Engineering News. Halford. Bethany. cen.acs.org. 2018-07-29.
  27. Carreira. Erick M.. Nannini. Leonardo J.. 2016-09-19. Synthesis of (+)-Psiguadial B. Synfacts. en. 12. 10. 1003. 10.1055/s-0036-1589189. 100560691 . 1861-1958.
  28. Farney. Elliot P.. Feng. Sean S.. Schäfers. Felix. Reisman. Sarah E.. 2018-01-31. Total Synthesis of (+)-Pleuromutilin. Journal of the American Chemical Society. 140. 4. 1267–1270. 10.1021/jacs.7b13260. 0002-7863. 5988231. 29323492.
  29. Cherney. Alan H.. Kadunce. Nathaniel T.. Reisman. Sarah E.. 2013-05-22. Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones. Journal of the American Chemical Society. 135. 20. 7442–7445. 10.1021/ja402922w. 23634932. 0002-7863.
  30. Repka. Lindsay M.. Ni. Jane. Reisman. Sarah E.. 2010-10-20. Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction. Journal of the American Chemical Society. 132. 41. 14418–14420. 10.1021/ja107328g. 0002-7863. 3222144. 20873714.
  31. Web site: Inhoffen Medal . 2024-03-28 . Helmholtz Centre for Infection Research . en.
  32. Web site: 2020 National Award Recipients Citations. 2020-09-06. American Chemical Society. en.
  33. Web site: Winner of the Women in Chemistry Award has been announced! – Thieme Chemistry – Georg Thieme Verlag KG. 2020-09-06. Thieme. en-GB.
  34. News: Lecture: "Necessity is the Mother of Invention: Natural Products and the Chemistry they Inspire". 2018-11-12. Mount Holyoke College. 2018-11-21. en.
  35. News: Gift Enables Transformative Advances in Health Care – Caltech Campaign. 2018-03-01. Caltech Campaign. 2018-11-17. en-US.
  36. 2015-09-23. Bright Young Minds: Meet 10 scientists who are making their mark. Science News. en. 188. 7. 20–26. 10.1002/scin.2015.188007018. 0036-8423.
  37. Book: Tetrahedron Young Investigator Award.
  38. Web site: Arthur C. Cope Scholar Awards – American Chemical Society. American Chemical Society. en. 2018-07-29.
  39. Web site: Arthur C. Cope Scholar: Sarah E. Reisman Chemical & Engineering News. Drahl. Carmen. cen.acs.org. 2018-07-26.
  40. Web site: Pasadena Now " Society Names Caltech Chemist Sarah Reisman a Rising Star Pasadena California, Hotels, CA Real Estate, Restaurants, City Guide... - Pasadena.com. www.pasadenanow.com. en. 2018-07-29.
  41. Web site: Women Chemists Committee announces inaugural Rising Star Award and winners – American Chemical Society. American Chemical Society. en. 2018-07-29.
  42. Web site: Sarah Reisman, Cottrell Scholar Award – Research Corporation for Science Advancement. Research Corporation for Science Advancement. 18 April 2012 . en. 2018-07-31.
  43. Web site: Novartis Early Career Award in Organic Chemistry 2012 :: News :: ChemistryViews. www.chemistryviews.org. 3 December 2012 . en. 2018-07-29.
  44. 2012-02-28. Boehringer Ingelheim New Investigator Award in organischer Chemie: A. G. Doyle / Boehringer Ingelheim New Faculty Grant: S. E. Reisman / GDCh-Preis für Schriftsteller und Journalisten: V. Köster. Angewandte Chemie. 124. 11. 2591. 10.1002/ange.201201128. 2012AngCh.124.2591. . 0044-8249.
  45. Web site: Past Fellows. sloan.org. 2018-07-29.
  46. Web site: NSF Award Search: Award#1057143 – CAREER: New Strategies and Methods for the Total Synthesis of Propellane Natural Products. www.nsf.gov. 2018-07-29.

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