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Sarah E. Reisman

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Sarah E. Reisman, Ph.D.
Alma materConnecticut College
Yale University
Scientific career
FieldsChemistry
Organic Chemistry
Natural product
InstitutionsCalifornia Institute of Technology
Harvard University
ThesisTotal synthesis of (+/-) Welwitindolinone A isonitrile (2006)
Doctoral advisorJohn L. Wood
Other academic advisorsEric Jacobsen

Sarah Elizabeth Reisman is a Professor of Chemistry at the California Institute of Technology and winner of an Arthur C. Cope Scholar Award and Tetrahedron Young Investigator Award for Organic Synthesis.[1]

Reisman's research focuses on the total synthesis of complex natural products.

Early career and education

Undergraduate Studies

Reisman received a B.A. in Chemistry from Connecticut College in 2001, conducting research in the lab of Prof. Timo V. Ovaska on the synthesis of tetracyclic terpenoid natural products, including phorbol.[2][3]

Graduate Studies

Reisman obtained her Ph.D. from Yale University in 2006, working with John L. Wood on the total synthesis of (±)-Welwitindolinone A Isonitrile.[4] Reisman's work included methodological developments towards a generalized skeleton, using nitrone cyclization and oxindole formation as linchpin transforms.

Postdoctoral Studies

Reisman was an NIH Postdoctoral Fellow in the lab of Eric N. Jacobsen at Harvard University and worked with Abigail Doyle to develop an enantioselective substitution of silyl ketenes onto an alkoxy chloride via an oxocarbenium ion, using a novel thiourea organocatalyst.[5]

Research

Reisman began her independent career as an Assistant Professor at Caltech in 2008 and was promoted to Full Professor in 2014.

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),[6][7] (–)-Maoecrystal Z,[8] (–)-8-Demethoxyrunanine, and (–)-Cepharatines A, C and D.[9] Their total synthesis of (+)-ryanodol was completed in 15 synthetic steps,[10] a significant improvement on the previous shortest synthetic route of 35 steps developed by Masayuki Inoue of the University of Tokyo.[11][12] In 2019, Reisman and coworkers published the first total synthesis of isoryanoid diterpene (+)-perseanol in Nature.[13] Other completed total syntheses include natural products (+)-Naseseazines A and B,[14] (+)-Salvileucalin B,[15] (+)-Psiguadial B[16][17][18] and (+)-Pleuromutilin.[19] The group's reaction methodology work has focused primarily on nickel catalysis,[20] cycloadditions,[21] and opening of strained-ring precursors.

Selected Awards and Honors

Reisman was awarded the Boehringer Ingelheim New Faculty Grant,[34] the Alfred P Sloan Foundation Fellowship[35] and a 5-year NSF CAREER Award in 2011.[36]

References

  1. ^ "The Reisman Group". reismangroup.caltech.edu. Retrieved 2018-07-26.
  2. ^ "Ovaska Research Group". Connecticut College. Retrieved 2018-07-26.
  3. ^ "Bright Young Minds: Meet 10 scientists who are making their mark". Science News. 188 (7): 20–26. 2015-09-23. doi:10.1002/scin.2015.188007018. ISSN 0036-8423.
  4. ^ 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" (PDF). Journal of the American Chemical Society. 130 (6): 2087–2100. doi:10.1021/ja076663z. ISSN 0002-7863. PMID 18198870.
  5. ^ Reisman, Sarah E.; Doyle, Abigail G.; Jacobsen, Eric N. (June 2008). "Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions". Journal of the American Chemical Society. 130 (23): 7198–7199. doi:10.1021/ja801514m. ISSN 0002-7863. PMC 2574628. PMID 18479086.
  6. ^ 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. 134 (4): 1930–1933. doi:10.1021/ja209354e. ISSN 0002-7863. PMC 3271125. PMID 22023250.
  7. ^ Drahl, Carmen. "Alkaloid Acetylaranotin Made After 40-Year Quest | Chemical & Engineering News". cen.acs.org. Retrieved 2018-07-29.
  8. ^ Cha, J. Y.; Yeoman, J. T. S.; Reisman, S. E. (2011-11-18). "Synthesis of (-)-Maoecrystal Z". Synfacts. 2011 (12): 14964–7. doi:10.1055/s-0031-1289337. ISSN 1861-1958. PMID 21877709.
  9. ^ Ley, Steven V.; Frost, James R. (2011-12-19). "Synthesis of (–)-8-Demethoxyrunanine and (–)-Cepharatines A, C and D". Synfacts. 8 (1): 0014. doi:10.1055/s-0031-1289924. ISSN 1861-1958.
  10. ^ Chuang, Kangway V.; Xu, Chen; Reisman, Sarah E. (2016-08-26). "A 15-step synthesis of (+)-ryanodol". Science. 353 (6302): 912–915. Bibcode:2016Sci...353..912C. doi:10.1126/science.aag1028. ISSN 0036-8075. PMC 5505075. PMID 27563092.
  11. ^ Lemonick, Sam. "A Simpler Way To Make A Complicated Molecule". Forbes. Retrieved 2018-07-26.
  12. ^ Pei-Qiang., Huang (2016). Efficiency in natural products total synthesis. [Place of publication not identified]: John Wiley & Sons. p. 132. ISBN 9781118940204. OCLC 1046102804.
  13. ^ Han, Arthur; Tao, Yujia; Reisman, Sarah E. (September 2019). "A 16-step synthesis of the isoryanodane diterpene (+)-perseanol". Nature. 573 (7775): 563–567. Bibcode:2019Natur.573..563H. doi:10.1038/s41586-019-1580-x. ISSN 1476-4687. PMC 7123484. PMID 31554978.
  14. ^ 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. 135 (15): 5557–5560. doi:10.1021/ja4023557. ISSN 0002-7863. PMC 3662218. PMID 23540731.
  15. ^ Levin, S.; Nani, R. R.; Reisman, S. E. (2011-05-19). "Enantioselective Synthesis of (+)-Salvileucalin B" (PDF). JACS. 133 (4): 774–6. doi:10.1021/ja110192b. PMID 21174417.
  16. ^ Chapman, Lauren M.; Beck, Jordan C.; Wu, Linglin; Reisman, Sarah E. (2016-08-02). "Enantioselective Total Synthesis of (+)-Psiguadial B" (PDF). Journal of the American Chemical Society. 138 (31): 9803–9806. doi:10.1021/jacs.6b07229. ISSN 0002-7863. PMID 27452034.
  17. ^ Halford, Bethany. "An enantioselective synthesis of (+)-psiguadial B | Chemical & Engineering News". cen.acs.org. Retrieved 2018-07-29.
  18. ^ Carreira, Erick M.; Nannini, Leonardo J. (2016-09-19). "Synthesis of (+)-Psiguadial B". Synfacts. 12 (10): 1003. doi:10.1055/s-0036-1589189. ISSN 1861-1958.
  19. ^ 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. doi:10.1021/jacs.7b13260. ISSN 0002-7863. PMC 5988231. PMID 29323492.
  20. ^ 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. doi:10.1021/ja402922w. ISSN 0002-7863.
  21. ^ 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. doi:10.1021/ja107328g. ISSN 0002-7863. PMC 3222144. PMID 20873714.
  22. ^ "2020 National Award Recipients Citations". American Chemical Society. Retrieved 2020-09-06.
  23. ^ "Winner of the Women in Chemistry Award has been announced! - Thieme Chemistry - Georg Thieme Verlag KG". Thieme. Retrieved 2020-09-06.
  24. ^ "Lecture: "Necessity is the Mother of Invention: Natural Products and the Chemistry they Inspire"". Mount Holyoke College. 2018-11-12. Retrieved 2018-11-21.
  25. ^ "Gift Enables Transformative Advances in Health Care - Caltech Campaign". Caltech Campaign. 2018-03-01. Retrieved 2018-11-17.
  26. ^ "Bright Young Minds: Meet 10 scientists who are making their mark". Science News. 188 (7): 20–26. 2015-09-23. doi:10.1002/scin.2015.188007018. ISSN 0036-8423.
  27. ^ Tetrahedron Young Investigator Award.
  28. ^ "Arthur C. Cope Scholar Awards - American Chemical Society". American Chemical Society. Retrieved 2018-07-29.
  29. ^ Drahl, Carmen. "Arthur C. Cope Scholar: Sarah E. Reisman | Chemical & Engineering News". cen.acs.org. Retrieved 2018-07-26.
  30. ^ "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. Retrieved 2018-07-29.
  31. ^ "Women Chemists Committee announces inaugural Rising Star Award and winners - American Chemical Society". American Chemical Society. Retrieved 2018-07-29.
  32. ^ "Sarah Reisman, Cottrell Scholar Award - Research Corporation for Science Advancement". Research Corporation for Science Advancement. Retrieved 2018-07-31.
  33. ^ "Novartis Early Career Award in Organic Chemistry 2012 :: News :: ChemistryViews". www.chemistryviews.org. Retrieved 2018-07-29.
  34. ^ "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. 2012-02-28. doi:10.1002/ange.201201128. ISSN 0044-8249.
  35. ^ "Past Fellows". sloan.org. Retrieved 2018-07-29.
  36. ^ "NSF Award Search: Award#1057143 - CAREER: New Strategies and Methods for the Total Synthesis of Propellane Natural Products". www.nsf.gov. Retrieved 2018-07-29.
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