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Stereoselective Desymmetrization Methods in the Assembly of Complex Natural Molecules (Springer Theses)

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en Limba Engleză Carte Hardback – 22 Jun 2016
This thesis describes the inception, design, and implementation of stereoselective desymmetrization reactions in the total synthesis of the natural products pactamycin and paspaline. In the case of pactamycin, the author develops a novel asymmetric Mannich reaction and symmetry-breaking reduction strategy to enable facile construction of the complex core architecture in fifteen steps using commercially available materials – the shortest synthesis to date. He subsequently demonstrates the flexibility of this approach in SAR investigations by highlighting the preparation of twenty-five unique pactamycin structural congeners. For paspaline, the author develops a biocatalytic desymmetrization strategy that allows the highly controlled synthesis of core stereochemistry and provides a platform for the development of new conceptual disconnections in the synthesis of "steroid-like" natural products. This thesis offers a valuable resource for students embarking on a PhD in total synthesis.
 

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Specificații

ISBN-13: 9783319390246
ISBN-10: 3319390244
Pagini: 381
Dimensiuni: 155 x 235 x 18 mm
Greutate: 5.68 kg
Ediția: 1st ed. 2016
Editura: Springer
Colecția Springer
Seria Springer Theses

Locul publicării: Cham, Switzerland

Cuprins

Asymmetric Synthesis Of The Aminocyclitol Pactamycin, A Universal Translocation Inhibitor.- Preparation And Biological Evaluation Of Synthetic and Polymer-Encapsulated Congeners of the Antitumor Agent Pactamycin: Insight Into Functional Group Effects and Biological Activity.- Inception and Development of a  Global and Local Desymmetrization Approach to the Synthesis of Steroidal Alkaloids: Stereocontrolled Total Synthesis of Paspaline.

Textul de pe ultima copertă

This thesis describes the inception, design, and implementation of stereoselective desymmetrization reactions in the total synthesis of the natural products pactamycin and paspaline. In the case of pactamycin, the author develops a novel asymmetric Mannich reaction and symmetry-breaking reduction strategy to enable facile construction of the complex core architecture in fifteen steps using commercially available materials – the shortest synthesis to date. He subsequently demonstrates the flexibility of this approach in SAR investigations by highlighting the preparation of twenty-five unique pactamycin structural congeners. For paspaline, the author develops a biocatalytic desymmetrization strategy that allows the highly controlled synthesis of core stereochemistry and provides a platform for the development of new conceptual disconnections in the synthesis of "steroid-like" natural products. This thesis offers a valuable resource for students embarking on a PhD in total synthesis.

Caracteristici

Includes detailed figures and schemes in each chapter and subsection to make the thesis easy to follow and understand

Provides extensive and thorough procedural and analytical information to allow the reader to easily replicate experimental conditions described in the thesis

Contains additional information and background not given in currently published literature to give enhanced perspective on the research performed