Synthesis of Substrates for Cyclization Studies Using Phenylselenium Ion and for Hydrovinylation Reactions
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Publisher:The Ohio State University
Series/Report no.:The Ohio State University. Department of Chemistry Honors Theses; 2010
Development of novel methods for making useful, enantiopure pharmaceutical compounds is an active area of current synthetic organic chemistry research. Many of these compounds contain heterocyclic components, which are ubiquitous in organic chemistry, but not always easy to synthesize. This project is aimed at making substrates for a reaction that utilizes a phenylselenium cation to induce an electrophilic cyclization by a heteroatom, thereby creating a heterocyclic compound. It is anticipated that this work will assist in the syntheses of pyrrolidinoindoline alkaloids such as physostigmine and the kinase inhibitor lyngbyatoxin. The use of the phenylselenium cation is found to have broad applications for the synthesis of diverse heterocycles that contain different leaving groups. Additionally, diverse vinylarene derivatives have been synthesized to explore the scope of the asymmetric hydrovinylation reactions. These include substrates for 2-arylpropionic acids (e. g., ibuprofen and naproxen) and also Frondosin B.