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Pure Appl. Chem., 2002, Vol. 74, No. 1, pp. 25-31

Toward the ideal synthesis. New transition metal-catalyzed reactions inspired by novel medicinal leads

Paul A. Wender, F. Christopher Bi, Gabriel G. Gamber, Francis Gosselin, Robert D. Hubbard, Marc J. C. Scanio, Robert Sun, Travis J. Williams and Lei Zhang

Department of Chemistry, Stanford University, Stanford, CA 94305, USA

Abstract: Studies in our laboratory are directed at the advancement of synthesis, biology, and medicine. This lecture will focus on new transition metal-catalyzed reactions that have been inspired by biologically potent targets such as phorbol and Taxol® and by the more general interest in producing syntheses that are concise, efficient, cost- and resource-effective, environmentally benign, quick, and simple to conductin essence, ideal. A special emphasis in our program is placed on new transition metal-catalyzed reactions that, in the absence of catalyst, would be forbidden or difficult to achieve. We have thus far reported the first examples of intramolecular metal-catalyzed [4+2], [5+2], and [4+4] cycloadditions, reactions that produce 6-, 7-, and 8-membered rings, respectively. Recent advances in our [5+2] cycloaddition studies will be presented, including new catalysts for relative and absolute stereochemical control. We will also describe recyclable catalysts that can be used in water, thereby minimizing cost and environmental concerns about solvent waste streams. New multicomponent reactions will also be presented. Finally, we will report a new [6+2] cycloaddition that produces an 8-membered ring.