A Novel Asymmetric Phase-Transfer Catalyzed Approach to the Compounds Ragaglitazar and Kuarsoin A

Authors

D. Karl Bedke, Brigham Young University

Keywords

asymmetric glycolate alkylation, alkoxyacetophenone, ragaglitazar, kuarsoin A

College

Physical and Mathematical Sciences

Department

Chemistry and Biochemistry

Abstract

Asymmetric glycolate alkylation plays a key role in the synthesis of complex biologically active compounds. Such asymmetric transformations have largely to date been accomplished by employing chiral auxiliaries which have shown remarkable success in asymmetric synthesis. However, auxiliaries must also be used in stoichiometric amounts and can become quite expensive. A catalytic approach to asymmetric glycolate alkylations presents an attractive option to the use of auxiliaries. Andrus2,3 et al. have recently developed a methodology utilizing phase-transfer catalyst 1 for alkylation of a novel alkoxyacetophenone substrate 2 that can be readily oxidized to its glycolic ester derivative to provide access to enantioenriched glycolic acid derivatives. To illustrate the utility of this methodology, two biologically active targets were selected and synthesized; their total syntheses are reported herein.

Recommended Citation

Bedke, D. Karl (2013) "A Novel Asymmetric Phase-Transfer Catalyzed Approach to the Compounds Ragaglitazar and Kuarsoin A," Journal of Undergraduate Research: Vol. 2013: Iss. 1, Article 2548.
Available at: https://scholarsarchive.byu.edu/jur/vol2013/iss1/2548