Abstract
Highly substituted carbocyclic and heterocyclic rings are key structural features in many biologically significant and commercially important compounds. Although classical synthetic approaches to such compounds have generally relied on linear substitution strategies, convergent cycloaddition and annulation strategies have emerged as powerful alternative methods for the assembly of highly substituted cyclic compounds. The intrinsic convergent nature of cycloaddition and annulation strategies facilitates the efficient assembly of highly substituted systems that would have required long, multistep routes using the alternative methods.
This talk will focus on the application of strained and unusual molecules as building blocks in cycloaddition strategies for the construction of complex carbocyclic and heterocyclic compounds. The synthetic utility of highly unsaturated, conjugated molecules such as vinylketenes, conjugated enynes, vinylallenes, allenylimines, and iminoacetonitriles will be described, as well as their application in the total synthesis of natural products.
About the speaker
Prof Rick Danheiser received his PhD from Harvard University in 1978. His doctoral research involved the first total synthesis of the diterpene plant growth hormone gibberellic acid. He joined the faculty of the Massachusetts Institute of Technology (MIT) in the same year, and is currently the Arthur C. Cope Professor of Chemistry.
Current investigations in Prof Danheiser’s laboratory involve the development of new strategies for the synthesis of complex molecules and their application in the total synthesis of natural products, and also the development of methods for the synthesis of polycyclic aromatic compounds with unusual spectroscopic and electronic properties. He is the editor-in-chief of Organic Syntheses, 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, Accounts of Chemical Research, and Chemistry Letters.
Prof Danheiser received numerous awards including the Stuart Pharmaceutical Award for Excellence in Chemical Research and the Cope Scholar Award of the American Chemical Society. He has been awarded an Alfred P. Sloan Foundation Fellowship. His educational contributions have been recognized with a MacVicar Faculty Fellowship, the MIT School of Science Prize for Excellence in Undergraduate Teaching, and the MIT Graduate Student Council Teaching Award.
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