The asymmetric total synthesis of (+)-geniposide via phosphine-catalyzed [3+2] cycloaddition

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The asymmetric total synthesis of (+)-geniposide via phosphine-catalyzed [3+2] cycloaddition

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Title: The asymmetric total synthesis of (+)-geniposide via phosphine-catalyzed [3+2] cycloaddition
Author: Jones, Regan Andrew
Abstract: The iridoids are a large family of monoterpenoid natural products that possess a wide range of biological activities. A great deal of research has already been done in the field of iridoid total synthesis, but limitations still remain. Specifically, few syntheses of iridoid β-glycosides have been reported. This work describes the 14 step asymmetric total synthesis of the iridoid β-glycoside (+)-geniposide utilizing a phosphine-catalyzed [3+2] cycloaddition as the key step. Other noteworthy steps in the synthesis include a palladium-catalyzed kinetic resolution and a previously unutilized method for iridoid glycosidation. In addition to describing the synthesis of (+)-geniposide, this dissertation will also review 1) phosphine-catalyzed cycloaddition reactions and 2) previous enantioselective total syntheses of iridoid glycosides.
Department: Chemistry and Biochemistry
Subject: Phosphine, Catalysis, [3+2] Cycloaddition, Synthesis, Iridoids
URI: http://hdl.handle.net/2152/ETD-UT-2009-05-16
Date: 2009-05

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