Doran, Robert.

Asymmetric Synthesis of Bioactive Lactones and the Development of a Catalytic Asymmetric Synthesis of α-Aryl Ketones [electronic resource] / by Robert Doran. - Cham : Springer International Publishing : Imprint: Springer, 2015. - XXI, 202 p. 258 illus., 3 illus. in color. online resource. - Springer Theses, Recognizing Outstanding Ph.D. Research, 2190-5053 . - Springer Theses, Recognizing Outstanding Ph.D. Research, .

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.

9783319205441

10.1007/978-3-319-20544-1 doi


Chemistry.
Organic chemistry.
Medicinal chemistry.
Catalysis.
Chemistry.
Organic Chemistry.
Catalysis.
Medicinal Chemistry.

QD415-436

547

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