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Synthetic studies towards homotyrosinol sulfonamide derivatives via Heck-Mizoroki coupling reactions

University of British Columbia

Homotyrosine, as a nonproteinogenic α-amino acid, is present as a component of diverse natural products that have important biological activities. Therefore, homotyrosine and its derivatives are important precursors for the total synthesis of some natural products. However, up to now, there was no report concerning a reliable synthetic route towards the synthesis of homotyrosine or its derivatives in a preparative scale. In this thesis, a robust method was developed for the preparation of homotyrosinol derivatives and related intermediates through a Mizoroki-Heck coupling reaction between an aryl iodide and appropriate amino acid-derived olefins in the presence of N-phenylurea as the ligand. In addition, a preparative scale protocol for the oxidative cyclization of the homotyrosinol sulfonamide derivative was established. These results are essential for various synthetic efforts towards more complicated natural products ongoing in our laboratory.

Text

2009-12-16

Attribution-NonCommercial-NoDerivatives 4.0 International

http://hdl.handle.net/2429/16838

Chemistry

University of British Columbia

UBCV

http://creativecommons.org/licenses/by-nc-nd/4.0/