Intramolecular Heck reactions in natural products total synthesis

ORGN 178

Larry E. Overman, leoverma@uci.edu, Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA 92697

 

Intramolecular Heck reactions have been employed extensively during the past 15 years as pivotal steps in total syntheses of a wide variety of polycyclic natural products. No other catalytic CC bond-forming reaction has found comparable wide application. A number of factors contribute to the broad utility of catalytic Heck cyclizations: predictable regioselectivity, high functional group tolerance, the success of catalytic asymmetric variants, the capacity to forge CC bonds in situations of considerable steric congestion, and the ability to form multiple rings in cascade processes.

Recently completed and ongoing total synthesis endeavors in my laboratories will be employed to illustrate the power of intramolecular Heck reactions for constructing natural products and other complex structures.