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Explorations with Sulfonyl Chemistry: Towards the Synthesis of the Natural Product Tedarene A and Cyclization Trials with Sulfonamide Derivatives

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Title: Explorations with Sulfonyl Chemistry: Towards the Synthesis of the Natural Product Tedarene A and Cyclization Trials with Sulfonamide Derivatives
Author: Lindner, Marshall
Department: Department of Chemistry
Program: Chemistry
Advisor: Schwan, Adrian
Abstract: Sulfones are capable of participating in a wide range of synthetic transformations including nucleophilic additions, acylations, alkylations and cycloadditions. A great deal of sulfone chemistry is derived from their ability to stabilize adjacent negative charges leading to stabilized α-carbanions. Previous work by the Schwan group investigated the base induced dearomatizing cyclization of unsaturated sulfones. An investigation into the cyclization of the analogous sulfonamide was explored. A route to the starting sulfonamide required for cyclization trials was not achieved and the project was abandoned. The synthesis of the natural product Tedarene A, a diaryl heptanoid was explored. Despite having no stereogenic centres Tedarene A exhibits planar chirality. A total synthesis of Tedarene A was presented using a minimal amount of organic starting materials featuring an Ullmann coupling. A total synthesis of Tedarene A was not accomplished, however with four steps remaining to achieve the desired product the progress made is reported.
URI: http://hdl.handle.net/10214/8818
Date: 2015-05


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