Alkenes are found in a great number of biologically active molecules and are employed in some of the most important transformations in organic chemistry. Catalytic procedures for stereoselective formation of alkenes are therefore highly valuable, and olefin metathesis offers what is likely the most attractive solution to this seminal problem.  In this lecture, mechanistic principles and design concepts that have resulted in the development of a variety of catalyst-controlled stereoselective olefin metathesis reactions will be presented; highly efficient and stereoselective cross-metathesis and macrocyclic ring-closing metathesis reactions will be emphasized. Concepts and principles that have led to the discovery of Mo-, W- as well as Ru-based catalysts in these laboratories for Z-selective olefin metathesis will be discussed.  The utility of the resulting catalysts and methods will be demonstrated in the context of synthesis of an assortment of biologically active molecules, such as an anti-oxidant plasmalogen phospholipid, immunostimulant KRN7000, antibacterial nakadomarin A, as well as anticancer agents epothilones A�D, cobretastain A4, falcarindiol, neopeltolide and disorazole C1.

Award Address  (ACS Award for Creative Work in Synthetic Organic Chemistry sponsored by Aldrich Chemical Company, LLC). New concepts, catalysts, and methods for stereoselective olefin metathesis

247th National Meeting (2014)

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