Rick L. Danheiser

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 organic reaction and Danheiser benzannulation chemical reaction.

Rick L. Danheiser
Born (1951-10-12) October 12, 1951
Alma materColumbia College (A.B.), Harvard University (Ph.D.)
Scientific career
FieldsOrganic chemistry, reproducibility in scientific research
Doctoral advisorE. J. Corey
Notable studentsJames Nowick
Websitehttp://danheiserlab.mit.edu

Education

Danheiser was born in New York and received his undergraduate education at Columbia College. 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").[1] and employed it in a total synthesis of the spiro sesquiterpene beta-vetivone.[2] 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.[3][4]

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;[5] 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");[6][7][8][9] benzannulation strategies based on pericyclic transformations of vinylketenes (“Danheiser Benzannulation”);[10][11] methods for the synthesis of aromatic and dihydroaromatic compounds based on cycloadditions of highly unsaturated conjugated molecules such as conjugated 1,3-enynes;[12] and formal [2 + 2 + 2] cycloadditions based on propargylic ene reaction/Diels-Alder cycloaddition cascades.[13] Natural products synthesized in his laboratory at MIT include the neurotoxic alkaloids anatoxin a[14] and quinolizidine 217A,[15] the immunosuppressant agent mycophenolic acid[16] the antitumor agent ascochlorin[17] 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.[18] He is a Fellow of the American Chemical Society.[19][20]

Teaching and service

Danheiser has a particular interest in reproducibility in scientific research.[21] 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.[22]

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".[23] 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.[24]

At MIT, Danheiser's educational contributions have been recognized with a MacVicar Faculty Fellowship,[25] the School of Science Prize for Excellence in Undergraduate Teaching,[26] the MIT Graduate Student Council Teaching Award, and the School of Science Prize for Graduate Education.[27]

References
  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. Kurti, L.; Czako, B. (2005). Strategic Applications of Named Reactions in Organic Synthesis. Elsevier Academic Press. pp. 124–125. ISBN 0-12-429785-4.
  8. Li, J. J. (2002). Name Reactions. Springer-Verlag. p. 90. ISBN 3-540-43024-5.
  9. Hassner, A.; Namboothiri, I. (2012). Name Reactions. Elsevier Academic Press. p. 112. ISBN 978-0-08-096630-4.
  10. 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.
  11. Kurti, L.; Czako, B. (2005). Strategic Applications of Named Reactions in Organic Synthesis. Elsevier Academic Press. pp. 122–124. ISBN 0-12-429785-4.
  12. 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.
  13. 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.
  14. 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.
  15. 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.
  16. 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.
  17. 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.
  18. "Arthur C. Cope Scholar Awards". American Chemical Society. Retrieved 19 March 2019.
  19. "2017 ACS Fellows". American Chemical Society. Retrieved 19 March 2019.
  20. "ACS National Award Winners". Chem. Eng. News. 72 (46): 49–54. 1994. doi:10.1021/cen-v072n046.p049.
  21. 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.
  22. 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.
  23. "SafetyStratus College and University Health and Safety Award". ACS Division of Chemical Health and Safety. Retrieved 19 March 2019.
  24. Prudent Practices in the Laboratory: Handling and Disposal of Chemicals. National Academies Press. 1995. doi:10.17226/4911. ISBN 978-0-309-21158-1.
  25. "MIT Names 3 MacVicar Fellows, Recognizing Outstanding Teaching". MIT News. Retrieved 19 March 2019.
  26. "Teaching prize recipients". MIT School of Science. Retrieved 19 March 2019.
  27. "School of Science announces winners of Teaching Prizes for Graduate and Undergraduate Education". MIT School of Science. Retrieved 19 March 2019.
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