Strategic use of pinacol-terminated Prins cyclizations in target-oriented total synthesis.
An important objective of contemporary synthesis endeavors is the development of new transformations that rapidly evolve molecular complexity in a stereocontrolled fashion. One approach toward this goal is to combine two or more distinct reactions into a single transformation, producing a process often referred to as a sequential, tandem, cascade, or domino reaction. In this Perspective, we discuss the development of one such tandem reaction, the acid-promoted (or catalyzed) Prins-pinacol rearrangement, with particular emphasis on its implementation as the key strategic element in the total synthesis of heterocyclic and carbocyclic natural products.
Overman
Larry E
LE
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA. leoverman@uci.edu
Pennington
Lewis D
LD