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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.
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.
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Fieser and Fieser's Reagents for Organic Synthesispp.358-359, (2017)
Fieser and Fieser's Reagents for Organic Synthesis (2017)
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Fieser and Fieser's Reagents for Organic Synthesispp.88-89, (2017)
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