Asymmetric Synthesis of Bioactive Lactones and the Development of a Catalytic Asymmetric Synthesis of α-Aryl Ketones [electronic resource] / by Robert Doran.

By: Doran, Robert [author.]Contributor(s): SpringerLink (Online service)Material type: TextTextSeries: Springer Theses, Recognizing Outstanding Ph.D. Research: Publisher: Cham : Springer International Publishing : Imprint: Springer, 2015Description: XXI, 202 p. 258 illus., 3 illus. in color. online resourceContent type: text Media type: computer Carrier type: online resourceISBN: 9783319205441Subject(s): Chemistry | Organic chemistry | Medicinal chemistry | Catalysis | Chemistry | Organic Chemistry | Catalysis | Medicinal ChemistryAdditional physical formats: Printed edition:: No titleDDC classification: 547 LOC classification: QD415-436Online resources: Texto completo
Contents:
Introduction to the Total Synthesis of Lactone-Containing Natural Products using ZrCl4 -- Asymmetric Synthesis of the β-Methyl-Substituted Analogues of (+)-Tanikolide and (–)-Malyngolide -- Asymmetric Synthesis of Both Enantiomers of a d-Lactone Analogue of Muricatacin -- Introduction to the Development of a Catalytic Asymmetric Synthesis of Tertiary α-Aryl Ketones -- A Stereoselective Switch: Enantiodivergent Approach to the Synthesis of Isoflavanones -- Asymmetric Synthesis of Tertiary α-Aryl Ketones by Decarboxylative Asymmetric Protonation.
In: Springer eBooksSummary: This thesis addresses two fundamental areas in contemporary organic chemistry: synthesis of natural products and catalytic asymmetric synthesis. Firstly, a new methodology, developed by our research group, which allows the asymmetric synthesis of lactones, a structural unit ubiquitous in natural products, was utilised in the synthesis of a number of natural product analogues that showed significant biological activity. Secondly, the development of a catalytic asymmetric synthesis of a key structural motif present in a number of natural products and pharmaceuticals was accomplished. During the course of this work we discovered dual stereocontrol, which is significant because it allows the configuration of a new stereocentre to be controlled by a simple change of proton source.
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Introduction to the Total Synthesis of Lactone-Containing Natural Products using ZrCl4 -- Asymmetric Synthesis of the β-Methyl-Substituted Analogues of (+)-Tanikolide and (–)-Malyngolide -- Asymmetric Synthesis of Both Enantiomers of a d-Lactone Analogue of Muricatacin -- Introduction to the Development of a Catalytic Asymmetric Synthesis of Tertiary α-Aryl Ketones -- A Stereoselective Switch: Enantiodivergent Approach to the Synthesis of Isoflavanones -- Asymmetric Synthesis of Tertiary α-Aryl Ketones by Decarboxylative Asymmetric Protonation.

This thesis addresses two fundamental areas in contemporary organic chemistry: synthesis of natural products and catalytic asymmetric synthesis. Firstly, a new methodology, developed by our research group, which allows the asymmetric synthesis of lactones, a structural unit ubiquitous in natural products, was utilised in the synthesis of a number of natural product analogues that showed significant biological activity. Secondly, the development of a catalytic asymmetric synthesis of a key structural motif present in a number of natural products and pharmaceuticals was accomplished. During the course of this work we discovered dual stereocontrol, which is significant because it allows the configuration of a new stereocentre to be controlled by a simple change of proton source.

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