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.
*Lecture presented at the 11th IUPAC International
Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
(OMCOS-11), Taipei, Taiwan, 22-26 July 2001. Other presentations are
presented in this issue, pp.1-186.
**Corresponding author.