CAREER: New Applications for Ortho-Quinone Methides in Organic Synthesis

University Of California-Santa Barbara, Santa Barbara CA

Investigators

Abstract

The objective of the proposed work is to investigate the use of ortho-quinone methides (o-QMs) as building blocks for organic synthesis. This study will begin with work on ways to use o-QMs to provide access to phenols which have been functionalized ortho to the hydroxy group. Ortho quinone methides are generated in situ and then trapped by 1,4 conjugate addition to directly provide functionalized phenols or trapped by 4 + 2 cycloaddition reactions. Asymmetric protocols for the 1,4 conjugate addition to o-QMs will then be developed and the adaptation of this o-QM chemistry to solid supports will be studied. The synthetic methodology developed in this project will be used in the syntheses of natural products, robustadial A, heliquinomycin and diinsininol. In this CAREER proposal, Dr. Pettus also presents ideas for modifications to the undergraduate organic chemistry lecture and laboratory classes at UCSB. With this CAREER award, the Organic and Macromolecular Chemistry Program is supporting the research and educational plans of Dr. Thomas R. Pettus of the Department of Chemistry at the University of California-Santa Barbara. Dr. Pettus will explore chemical reactions of compounds which contain a functional group (reactive site) known as an ortho-quinone methide (o-QM). Ortho-quinone methides can be generated in situ and then used to produce a variety of aromatic compounds which have heretofore been difficult to make. The synthetic methodology developed in this project will be used in the syntheses of natural products, robustadial A, heliquinomycin and diinsininol. These natural products posess a wide range of biological activities. Students trained during the course of this research work will gain skills needed by the pharmaceutical and speciality chemicals industries. In this CAREER proposal, Dr. Pettus also presents ideas for modifications to the undergraduate organic chemistry lecture and laboratory classes at UCSB.