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Rick L. Danheiser

From Wikipedia, the free encyclopedia

Rick L. Danheiser
Born (1951-10-12) October 12, 1951 (age 72)
Alma materColumbia College (A.B.), Harvard University (Ph.D.)
Scientific career
FieldsOrganic chemistry, Reproducibility in Scientific Research
ThesisThe Total Synthesis of Gibberellic Acid (1978)
Doctoral advisorE. J. Corey
Other academic advisorsGilbert Stork
Notable studentsJames Nowick
Websitedanheiserlab.mit.edu

Rick L. Danheiser is an American organic chemist and is the Arthur C. Cope Professor of Chemistry at the Massachusetts Institute of Technology and chair of the MIT faculty. His research involves the invention of new methods for the synthesis of complex organic compounds. Danheiser is known for the Danheiser annulation and Danheiser benzannulation reactions.

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Transcription

PHIL: One person is going to win, and they can choose to bring along somebody of their choice. [MUSIC PLAYING] NARRATOR: Last time in 5.301, the students just practiced re-crystallization. Now it's time for the real thing. PROFESSOR: You're actually going to take your crystals, and you're going to re-crystallize them, to produce one big crystal. And there's a prize. Whoever gets this first is going to lunch with me at Legal Sea Foods, and you can bring one of your friends, and you can invite the TAs. NARRATOR: The goal is to grow a single, perfect, crystal. But first, the students have to actually make the compound they're going to grow their crystals from, this chromium complex. This is their first real reaction in the lab. ANTHONY: It's a different color and that's usually pretty good in chemistry. NARRATOR: After they filter, wash, and dry their product, the students begin testing solvents, and some start teaming up. PHIL: I actually saw an alliance forming over here. YI-SHIUAN: I saw some of them split up trying different solvents. We actually worked on find the solvents together. JULIE: We decided to use dichloromethane and hexane for our solvents. ANTHONY: We're going to use hexanes and methanol. Shh. We're going to win. NARRATOR: Hansol seems pretty driven. HANSOL: I like competition. I want to win, obviously. NARRATOR: If you win, who will you invite to lunch? HANSOL: I would probably pick Dan. I made a deal with him earlier. NARRATOR: So, Hansol's been working with Dan. What about you, Emily? EMILY: Yeah, I worked with Dan to figure out what solvent system would work well. NARRATOR: Uh, OK. Let's recap. HANSOL: Dan. EMILY: Dan. HANSOL: Dan. EMILY: Dan HANSOL: Dan. EMILY: Dan. NARRATOR: Dan, what do you have to say for yourself? DAN: It was a loosely formed alliance, we didn't sign any papers. NARRATOR: Ike meanwhile has a different idea. IKE: I'm broke. If I get the ticket I'm going to sell it for money. Because I know, these suckers want it really bad. PHIL: We have some people whose samples look pretty good. They seem to be wanting to try a lot of different solvent systems, a lot of different temperatures. They're asking a lot of questions. They want to make sure that everything is perfect. Because I think everyone wants to get the biggest crystal. They're very determined. They're going for all or nothing. They don't want a bunch of small crystals. LINA: Next week, we're going to win the biggest crystal competition. Because the winners get to take the TAs and Professor Dolhun out to lunch. JULIE: Legal Sea Foods, for free. NARRATOR: So that's it. Everything's set and everyone's excited about the prize. But, who will win? Find out next time on 5.301. JULIE: Yeah, we're done. PHIL: I'm having this re-occurring dream. It's like I'm jogging through a park with a fitness boot camp. And I stop to talk to Kris Jenner. And I always say, no, no, no, Kris, I can't talk to you right now. And she pours Kool-Aid on me. And I wake up drenched in Kool-Aid. That's a dream. If it was Bruce Jenner pouring Kool-Aid on me, that would be a nightmare. [MUSIC PLAYING]

Education

Danheiser was born in New York and received his B.A. in 1972 at Columbia College.[1] While working as an undergraduate under the direction of Gilbert Stork, Danheiser developed a method for the regiospecific alkylation of beta-diketone enol ethers (the "Stork-Danheiser Alkylation").[2] and employed it in a total synthesis of the spiro sesquiterpene beta-vetivone.[3] Danheiser received his Ph.D. at Harvard University in 1978. His doctoral research (under the direction of E. J. Corey) involved the first total synthesis of the diterpene plant growth hormone gibberellic acid.[4][5][6]

Research

Danheiser's research has focused on the development of new strategies for the synthesis of complex molecules and their application in the total synthesis of natural products. Synthetic methods invented in his laboratory include highly stereoselective [4 + 1] cyclopentene annulations based on oxyanion and carbanion-accelerated vinylcyclopropane rearrangements;[7] the application of organosilanes (e.g., allenylsilanes, propargylsilanes, and allylsilanes) in a general [3 + 2] annulation strategy for the synthesis of five-membered carbocycles and heterocycles (the "Danheiser Annulation");[8][9][10][11] benzannulation strategies based on pericyclic transformations of vinylketenes (“Danheiser benzannulation”);[12][13] methods for the synthesis of aromatic and dihydroaromatic compounds based on cycloadditions of highly unsaturated conjugated molecules such as conjugated 1,3-enynes;[14] and formal [2 + 2 + 2] cycloadditions based on propargylic ene reaction/Diels-Alder cycloaddition cascades.[15] Natural products synthesized in his laboratory at MIT include the neurotoxic alkaloids anatoxin a[16] and quinolizidine 217A,[17] the immunosuppressant agent mycophenolic acid[18] the antitumor agent ascochlorin[19] and a number of diterpene quinones derived from the Chinese traditional medicine Dan Shen.

Notable research awards

Danheiser was awarded the Cope Scholar Award of the American Chemical Society in 1995.[20] He is a Fellow of the American Chemical Society.[21][22]

Teaching and service

Danheiser has a particular interest in reproducibility in scientific research.[23] He has been the editor-in-chief of the journal Organic Syntheses and a member of the board of directors of the Organic Syntheses corporation since 2004. Organic Syntheses has the unusual feature that all data and experiments reported in articles must be confirmed in the laboratory of a member of the editorial board prior to publication.[24]

Danheiser has a longstanding interest in laboratory safety and at MIT he has served as the chair of several committees including the MIT Chemistry Department EHS Committee which was recognized in 1991 as the first recipient of the American Chemical Society Division of Chemical Safety national award for "best university safety program".[25][failed verification] Danheiser also served on the National Research Council Committee on Prudent Practices for the Handling, Storage and Disposal of Chemicals in Laboratories, chairing the Subcommittee on Assessing Chemical Hazards.[26]

At MIT, Danheiser's educational contributions have been recognized with a MacVicar Faculty Fellowship,[27] the School of Science Prize for Excellence in Undergraduate Teaching,[28] the MIT Graduate Student Council Teaching Award, and the School of Science Prize for Graduate Education.[29]

References

  1. ^ Danheiser, Rick L. "Rick Lane Danheiser A C Cope Professor of Chemistry." Chemistry Directory. MIT, Web. 23 Nov. 2014.
  2. ^ Stork, G.; Danheiser, R. L. (1973). "The Regiospecific Alkylation of Cyclic b Diketone Enol Ethers. A General Synthesis of 2-Alkylcyclohexenones". J. Org. Chem. 38 (9): 1775–1776. doi:10.1021/jo00949a048.
  3. ^ Stork, G.; Danheiser, R. L.; Ganem, B. (1973). "Spiroannelation of Enol Ethers of Cyclic 1,3-Diketones. A Simple Stereospecific Synthesis of -Vetivone". J. Am. Chem. Soc. 95 (10): 3414–3415. doi:10.1021/ja00791a074.
  4. ^ Corey, E. J.; Danheiser, R. L.; Chandrasekaran, S.; Siret, P.; Keck, G. E.; Gras, J.-L. (1978). "Stereospecific Total Synthesis of Gibberellic Acid. A Key Tricyclic Intermediate". J. Am. Chem. Soc. 100 (25): 8031. doi:10.1021/ja00493a055.
  5. ^ Corey, E. J.; Danheiser, R. L.; Chandrasekaran, S.; Keck, G. E.; Gopalan, B.; Larsen, S. D.; Siret, P.; Gras, J.-L. (1978). "Stereospecific Total Synthesis of Gibberellic Acid". J. Am. Chem. Soc. 100 (25): 8034. doi:10.1021/ja00493a055.
  6. ^ Jandh. "Rick L. Danheiser Details." Chemistry Tree, 11 Dec. 2011. Web. 23 Nov. 2014.
  7. ^ Danheiser, R. L.; Bronson, J. J.; Okano, K. (1985). "The Carbanion-Accelerated Vinylcyclopropane Rearrangement. Application in a General, Stereocontrolled Annulation Approach to Cyclopentene Derivatives". J. Am. Chem. Soc. 107 (15): 4579. doi:10.1021/ja00301a051.
  8. ^ Danheiser, R. L.; Carini, D. J.; Basak, A. (1981). "TMS-Cyclopentene Annulation: A Regiocontrolled Approach to the Synthesis of Five-Membered Rings". J. Am. Chem. Soc. 103 (6): 1604. doi:10.1021/ja00301a051.
  9. ^ Kurti, L.; Czako, B. (2005). Strategic Applications of Named Reactions in Organic Synthesis. Elsevier Academic Press. pp. 124–125. ISBN 0-12-429785-4.
  10. ^ Li, J. J. (2002). Name Reactions. Springer-Verlag. p. 90. ISBN 3-540-43024-5.
  11. ^ Hassner, A.; Namboothiri, I. (2012). Name Reactions. Elsevier Academic Press. p. 112. ISBN 978-0-08-096630-4.
  12. ^ Danheiser, R. L.; Gee, S. K. (1984). "A Regiocontrolled Annulation Approach to Highly Substituted Aromatic Compounds". J. Org. Chem. 49 (9): 1672. doi:10.1021/jo00183a043.
  13. ^ Kurti, L.; Czako, B. (2005). Strategic Applications of Named Reactions in Organic Synthesis. Elsevier Academic Press. pp. 122–124. ISBN 0-12-429785-4.
  14. ^ Danheiser, R. L.; Gould, A. E.; Fernandez de la Pradilla, R.; Helgason, A. L. (1994). "Intramolecular [4 + 2] Cycloaddition Reactions of Conjugated Enynes". J. Org. Chem. 59 (19): 5514. doi:10.1021/jo00098a002.
  15. ^ Sakai, T.; Danheiser, R. L. (2010). "Cyano Diels-Alder and Cyano Ene Reactions. Applications in a Formal [2 + 2 +2] Cycloaddition Strategy for the Synthesis of Pyridines". J. Am. Chem. Soc. 132 (38): 13203–13205. doi:10.1021/ja106901u. PMC 2944912. PMID 20815385.
  16. ^ Danheiser, R. L.; Morin, J. M.; Salaski, E. J. (1985). "An Efficient Total Synthesis of Anatoxin a". J. Am. Chem. Soc. 107 (26): 8066. doi:10.1021/ja00312a045.
  17. ^ Maloney, K. M.; Danheiser, R. L. (2005). "Total Synthesis Quinolizidine Alkaloid (-)-217A. Application of Iminoacetonitrile Cycloadditions in Organic Synthesis". Org. Lett. 7 (14): 3115–3118. doi:10.1021/ol051185n. PMC 3203637. PMID 15987219.
  18. ^ Danheiser, R. L.; Gee, S. K.; Perez, J. J. (1986). "The Total Synthesis of Mycophenolic Acid". J. Am. Chem. Soc. 108 (4): 806. doi:10.1021/ja00264a038.
  19. ^ Dudley, G. B.; Takaki, K. S.; Cha, D. D.; Danheiser, R. L. (2000). "Total Synthesis of (-)-Ascochlorin via a Cyclobutenone-Based Benzannulation Strategy". Org. Lett. 2 (21): 3407–10. doi:10.1021/ol006561c. PMID 11029223.
  20. ^ "Arthur C. Cope Scholar Awards". American Chemical Society. Retrieved 19 March 2019.
  21. ^ "2017 ACS Fellows". American Chemical Society. Retrieved 19 March 2019.
  22. ^ "ACS National Award Winners". Chem. Eng. News. 72 (46): 49–54. 1994. doi:10.1021/cen-v072n046.p049.
  23. ^ Bergman, R. G.; Danheiser, R. L. (2016). "Reproducibility in Chemical Research" (PDF). Angew. Chem. Int. Ed. 55 (41): 12548–12549. doi:10.1002/anie.201606591. hdl:1721.1/114628. PMID 27558212.
  24. ^ Danheiser, R. L. (2011). "Organic Syntheses: The 'Gold Standard' in Experimental Synthetic Organic Chemistry". Org. Synth. 88: 1–3. doi:10.15227/orgsyn.088.0001.
  25. ^ "SafetyStratus College and University Health and Safety Award". ACS Division of Chemical Health and Safety. Retrieved 19 March 2019.
  26. ^ Prudent Practices in the Laboratory: Handling and Disposal of Chemicals. National Academies Press. 1995. doi:10.17226/4911. ISBN 978-0-309-21158-1.
  27. ^ "MIT Names 3 MacVicar Fellows, Recognizing Outstanding Teaching". MIT News. 2 February 1996. Retrieved 19 March 2019.
  28. ^ "Teaching prize recipients". MIT School of Science. Retrieved 19 March 2019.
  29. ^ "School of Science announces winners of Teaching Prizes for Graduate and Undergraduate Education". MIT School of Science. Retrieved 19 March 2019.
This page was last edited on 13 April 2024, at 12:25
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