Rick Danheiser grew up in New York and California and 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 ß-diketone enol ethers (the "Stork-Danheiser
Alkylation") and employed it in a total synthesis of the spiro
sesquiterpene ß-vetivone.
Professor Danheiser received his Ph.D. at Harvard
University in 1978. His doctoral research (under the direction of
Professor 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; and methods for the synthesis of aromatic
and dihydroaromatic compounds based on cycloadditions of highly unsaturated
conjugated molecules such as conjugated 1,3-enynes. 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 current 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. At MIT, Dr. Danheiser's
educational contributions have been recognized with a MacVicar
Faculty Fellowship, the School of Science Prize for Excellence in
Undergraduate Teaching, and the MIT Graduate
Student Council Teaching Award. Professor Danheiser is the Editor-in-Chief
of Organic Syntheses,
has served as an editor of the "Encyclopedia of Reagents for Organic
Synthesis", and is as a member of the Editorial Advisory Boards
of Organic
Letters, Accounts
of Chemical Research, and Chemistry
Letters. In collaboration with Professor William Roush, Dr.
Danheiser has 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 fifteen years.
Professor Danheiser
has a special 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 has also served on the National Research
Council Committee on Prudent Practices for the Handling, Storage, and
Disposal of Chemicals in Laboratories and chaired the Subcommittee on
Assessing Chemical Hazards.
