Rick L. Danheiser

Arthur C. Cope Professor of Chemistry

Massachusetts Institute of Technology
Cambridge, Massachusetts

Dr. Rick Danheiser received his undergraduate education at Columbia College. While working as an undergraduate under the direction of Professor Gilbert Stork, Dr. Danheiser developed a method for the regiospecific alkylation of β-diketone enol ethers (the “Stork-Danheiser Alkylation”) and employed it in a total synthesis of the spiro sesquiterpene β-vetivone. Professor 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.

Dr. Danheiser joined the faculty of the Massachusetts Institute of Technology in 1978 and at present is the Arthur C. Cope Professor of Chemistry. Current investigations in his laboratory involve the development of new strategies for the synthesis of complex molecules and their application in the total synthesis of natural products. Synthetic methods previously invented in his laboratory include highly stereoselective [4+1] cyclopentene annulations based on oxyanion and carbanion-accelerated vinylcyclopropane rearrangements; 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”); a [4+4] annulation route to eight-membered carbocycles based on a cascade of pericyclic reactions; benzannulation strategies based on pericyclic transformations of vinylketenes (“Danheiser Benzannulation”); methods for the synthesis of aromatic and dihydroaromatic compounds based on cycloadditions of highly unsaturated conjugated molecules such as conjugated 1,3-enynes; and formal [2+2+2] cycloadditions based on propargylic ene reaction/Diels-Alder cycloaddition cascades. Natural products synthesized in his laboratory at MIT include the neurotoxic alkaloids anatoxin a and quinolizidine 217A, the immunosuppressant agent mycophenolic acid, the host defense stimulant maesanin, the antitumor agent ascochlorin, and a number of diterpene quinones derived from the Chinese traditional medicine Dan Shen.

Another focus of research in the Danheiser laboratory involves the development of methods for the synthesis of polycyclic aromatic compounds with unusual spectroscopic and electronic properties. Recent studies have led to efficient new strategies for the synthesis of azulenes, phenalenones, and cyclopenta[a]phenalenes. “Green chemistry” represents another area of interest in the Danheiser group. Investigations in this area include the development of environmentally friendly methods for organic synthesis using water and carbon dioxide as reaction media, and the total synthesis of semiochemicals with potential utility as environmentally benign pest control agents.

Honors awarded to Professor Danheiser include an Alfred P. Sloan Foundation Fellowship, the Stuart Pharmaceutical Award for Excellence in Chemical Research, and the Cope Scholar Award of the American Chemical Society. In 2017 Professor Danheiser was named a Fellow of the American Chemical Society. Professor Danheiser is the Editor-in-Chief of Organic Syntheses and a member of the Board of Directors of the Organic Syntheses corporation, has served as an editor of the “Encyclopedia of Reagents for Organic Synthesis”, and is a member of the Editorial Advisory Boards of Organic Letters, The Chemical Record, and Chemistry Letters.

At MIT, Dr. Danheiser’s educational contributions have been recognized with a MacVicar Faculty Fellowship, both the School of Science Prize for Excellence in Undergraduate Education (1998) and the School of Science Prize for Graduate Education (2014), and the MIT Graduate Student Council Teaching Award. Professor Danheiser served as Associate Department Head of the Department of Chemistry at MIT from 1995-2005 and in that capacity had responsibility for directing both the undergraduate and graduate programs in the department. In 1997, Professor Danheiser served as Acting Department Head of the MIT Chemistry Department. Professor Danheiser was elected to a two-year term as Associate Chair of the MIT Faculty in 2017, and in 2018 was elected by the Faculty to become the Chair of the Faculty effective in July 2019.

In collaboration with Professor William Roush, Dr. Danheiser developed an intensive “short course” on “Recent Advances in Organic Synthesis Methodology” which has been presented at more than twenty-five companies in the U.S. and Europe during the past twenty years.

Professor Danheiser’s service to the scientific community includes organizing a number of conferences and symposia including symposia at five Pacifichem Conferences and serving as the Chair of the Gordon Research Conference on Natural Product in 1995. Professor Danheiser has a longstanding interest in laboratory safety and at MIT he currently serves as the Chair of the Chemistry Department Environmental Health and Safety Committee and as Chair of the MIT Committee on Toxic Chemicals. In 1991, the MIT Chemistry Department was honored as the first recipient of the American Chemical Society’s national award for “best university safety program”. Dr. 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. In recent years Professor Danheiser has served as a consultant for several universities on matters involving laboratory safety.