Brian Stoltz

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Brian Stoltz
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Born
Brian M. Stoltz

(1970-11-12) November 12, 1970 (age 51)
Nationality American
Alma mater Indiana University of Pennsylvania (B.S., 1993)
Yale (Ph.D., 1997)
Awards Fellow of the American Association for the Advancement of Science
Scientific career
Fields Chemistry
Institutions California Institute of Technology
Doctoral advisor John L. Wood
Other academic advisors E. J. Corey
Doctoral students
Website www.cce.caltech.edu/content/brian-m-stoltz OOjs UI icon edit-ltr-progressive.svg

Brian M. Stoltz is currently a professor of chemistry at the California Institute of Technology. [2] The primary focus of his research is chemical synthesis with an emphasis on expanding the scope of allylic alkylation for the preparation of complex molecules possessing unique structural, biological, and physical properties. His research involves the total synthesis of natural products such as dragmacidin F [3] and (–)-cyanthiwigin F, [4] and development of synthetic reactions to access quaternary stereocenters. [5] Specifically, he has focused on the allylic alkylation of enolates, developing an enantioselective variant in 2004. [6]

Contents

Education

Stoltz received undergraduate degrees in Chemistry and German from Indiana University of Pennsylvania in 1993. As an undergraduate he spent a year abroad at the Ludwig Maximilian University of Munich. He went on to earn his M.S. and Ph.D. at Yale University, where he studied organic chemistry under the supervision of John L. Wood, completing his studies in 1997. Upon completion of his graduate work, he held an NIH post-doctoral fellowship appointment in the laboratory of E. J. Corey at Harvard University from 1998 to 2000.

Career and research

Stoltz is the Editor-in-Chief of Tetrahedron. At present[ when? ] he is also an associate editor for the Beilstein Journal of Organic Chemistry . [7]

Awards and honors


Related Research Articles

Elias James Corey American chemist (born 1928)

Elias James Corey is an American organic chemist. In 1990, he won the Nobel Prize in Chemistry "for his development of the theory and methodology of organic synthesis", specifically retrosynthetic analysis. Regarded by many as one of the greatest living chemists, he has developed numerous synthetic reagents, methodologies and total syntheses and has advanced the science of organic synthesis considerably.

Enamine

An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates.

Corey–Itsuno reduction

The Corey–Itsuno reduction, also known as the Corey–Bakshi–Shibata (CBS) reduction, is a chemical reaction in which an achiral ketone is enantioselectively reduced to produce the corresponding chiral, non-racemic alcohol. The oxazaborolidine reagent which mediates the enantioselective reduction of ketones was previously developed by the laboratory of Itsuno and thus this transformation may more properly be called the Itsuno-Corey oxazaborolidine reduction.

The Carroll rearrangement is a rearrangement reaction in organic chemistry and involves the transformation of a β-keto allyl ester into a α-allyl-β-ketocarboxylic acid. This organic reaction is accompanied by decarboxylation and the final product is a γ,δ-allylketone. The Carroll rearrangement is an adaptation of the Claisen rearrangement and effectively a decarboxylative allylation.

Chiral auxiliary

A chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically recovered for future use.

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Larry E. Overman

Larry E. Overman is Distinguished Professor of Chemistry at the University of California, Irvine. He was born in Chicago in 1943. Overman obtained a B.A. degree from Earlham College in 1965, and he completed his Ph.D. in chemistry from the University of Wisconsin–Madison in 1969, under Howard Whitlock Jr. Professor Overman is a member of the United States National Academy of Sciences and the American Academy of Arts and Sciences. He was the recipient of the Arthur C. Cope Award in 2003, and he was awarded the Tetrahedron Prize for Creativity in Organic Chemistry for 2008.

Horsfiline Chemical compound

Horsfiline is an oxindole alkaloid found in the plant Horsfieldia superba, which is used in traditional herbal medicine. It has analgesic effects and has been the subject of research both to produce it synthetically by convenient routes and to develop analogues and derivatives which may have improved analgesic effects.

The Tsuji–Trost reaction is a palladium-catalysed substitution reaction involving a substrate that contains a leaving group in an allylic position. The palladium catalyst first coordinates with the allyl group and then undergoes oxidative addition, forming the π-allyl complex. This allyl complex can then be attacked by a nucleophile, resulting in the substituted product.

Phosphinooxazolines

Phosphinooxazolines are a class of chiral ligands used in asymmetric catalysis. Their complexes are particularly effective at generating single enatiomers in reactions involving highly symmetric transition states, such as allylic substitutions, which are typically difficult to perform stereoselectively. The ligands are bidentate and have been shown to be hemilabile with the softer P‑donor being more firmly bound than the harder N‑donor.

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Abigail Gutmann Doyle is a Professor of Chemistry at the University of California, Los Angeles, where she holds the Saul Winstein Chair in Organic Chemistry. Her research focuses on the development of new chemical transformations in organic chemistry.

Sarah Elizabeth Reisman is a Chemistry Professor at the California Institute of Technology. She received the (2013) Arthur C. Cope Scholar Award and the (2014) Tetrahedron Young Investigator Award for Organic Synthesis. Her research focuses on the total synthesis of complex natural products.

Michael J. Krische American chemist and Robert A (born 1966)

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Richmond Sarpong is a Ghanaian-American chemist who is a professor at the University of California, Berkeley. Sarpong works on natural product total synthesis to better understand biological systems and allow for the development of novel therapeutics. He was awarded a Guggenheim Fellowship in 2017, and was elected a fellow of the American Association for the Advancement of Science in 2020. He serves on the editorial boards of Organic Syntheses, Accounts of Chemical Research and Synlett.

Teruaki Mukaiyama Japanese chemist

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Jin-Quan Yu is a Chinese-born American chemist. He is the Frank and Bertha Hupp Professor of Chemistry at Scripps Research, where he also holds the Bristol Myers Squibb Endowed Chair in Chemistry. He is a 2016 recipient of the MacArthur Fellowship, and is a member of the American Academy of Arts and Sciences, American Association for the Advancement of Science, and the Royal Society of Chemistry. Yu is a leader in the development of C–H bond activation reactions in organic chemistry, and has reported many C–H activation reactions that could be applicable towards the synthesis of drug molecules and other biologically active compounds. He also co-founded Vividion Therapeutics in 2016 with fellow Scripps chemists Benjamin Cravatt and Phil Baran, and is a member of the scientific advisory board of Chemveda Life Sciences.

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References

  1. Nelson, Hosea (2013). A Unified Synthetic Approach to the Transtaganolide and Basiliolide Natural Products. caltech.edu (PhD thesis). California Institute of Technology. doi:10.7907/09DW-P586. OCLC   1014495702.
  2. "Brian M. Stoltz". stoltz.caltech.edu. Archived from the original on July 9, 2015. Retrieved August 19, 2015.
  3. Garg, Neil K.; Caspi, Daniel D.; Stoltz, Brian M. (July 20, 2004). "The Total Synthesis of (+)-Dragmacidin F" (PDF). Journal of the American Chemical Society. 126 (31): 9552–9553. doi:10.1021/ja046695b. PMID   15291554.
  4. Enquist, John A.; Stoltz, Brian M. (May 2, 2008). "The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation". Nature. 453 (7199): 1228–1231. Bibcode:2008Natur.453.1228E. doi:10.1038/nature07046. PMC   2474750 . PMID   18580947.
  5. "Press release: Potassium Salt Outperforms Precious Metals As a Catalyst | Caltech". The California Institute of Technology. February 4, 2015.
  6. Stoltz, Brian; Behenna, Douglas (October 28, 2004). "The Enantioselective Tsuji Allylation" (PDF). J. Am. Chem. Soc. 126 (46): 15044–15045. doi:10.1021/ja044812x. PMID   15547998.
  7. Beilstein Journal of Organic Chemistry Prof. Brian M. Stoltz
  8. "American Chemical Society, Award for Creative Work in Synthetic Organic Chemistry". C&En Global Enterprise. acs.org. 96 (2): 49. 8 January 2018. doi:10.1021/cen-09602-awards50 . Retrieved February 16, 2020.
  9. "NSF Award Recipient Details". nsf.gov. Retrieved August 31, 2015.
  10. "Past Laureates of the Raymond and Beverly Sackler International Prize in the Physical Sciences". 5 September 2012.
  11. "Elias J. Corey Award for Outstanding Original Contribution in Organic Synthesis by a Young Investigator" . Retrieved September 3, 2015.
  12. "Alumnus Stoltz Honored with Tetrahedron Young Investigator Award". iup.edu. February 24, 2010. Retrieved August 31, 2015.
  13. "Brian Stoltz Receives 2015 Mukaiyama Award". caltech.edu. October 1, 2014. Archived from the original on March 17, 2015. Retrieved August 31, 2015.