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Total Synthesis of (±)-Maoecrystal V

Total Synthesis of (±)-Maoecrystal V
Author: Jianxian Gong
Publisher: Springer
Total Pages: 146
Release: 2014-07-08
Genre: Science
ISBN: 3642543049

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In this thesis, the author describes the total synthesis of natural product Maoecrystal V in detail. In the first part of the thesis, the author introduces the research background and reviews the research progress in total synthesis of Maoecrystal V. In the second part, the author develops a novel and concise approach for the stereo selective construction of the tetracyclic model system of Maoecrystal V. The model system is accomplished in 8 steps with 20% yield. In the third part, the author describes the first successful total synthesis of Maoecrystal V and investigates four strategies for constructing the key tetrahydrofuran oxa-bridge skeleton. The total synthesis starts from a known compound and is accomplished in 17 steps with 1.2% yield. The successful total synthesis of Maoecrystal V will contribute to the development of efficient synthetic strategies for natural products and other compounds with complex structures.


Total Synthesis of Maoecrystal V

Total Synthesis of Maoecrystal V
Author: Feng Peng
Publisher:
Total Pages:
Release: 2012
Genre:
ISBN:

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This thesis describes in detail our journey toward Maoecrystal V, a potential anti-cancer diterpenoid. Maoecrsytal V was isolated in 2004 from a Chinese herbal medicine. It has a highly congested structure, in which there are three continuous quaternary carbon center embedded within a rigid pentacyclic scaffold. The first chapter of this thesis covers the isolation, bioactivity, and synthetic efforts from other groups. The second chapter discusses our first generation strategy toward Maoecrystal V. During our early studies, we successfully found the conditions for the key intramolecular Diels-Alder reaction. We also identified that the facial selectivity of this Diels-Alder reaction is a big challenge for our synthesis plan. The third chapter describes our solution to the core structure of Maoecrystal V. The exploration resulted in the discovery of a novel exo-glycal epoxide rearrangement. The last chapter describes the total synthesis of Maoecrystal V. The difficulties we met and our solution is discussed.


Studies Toward the Total Synthesis of Maoecrystal V

Studies Toward the Total Synthesis of Maoecrystal V
Author: Paul John Krawczuk
Publisher:
Total Pages: 632
Release: 2011
Genre: Diterpenes
ISBN:

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In 2004, Li and coworkers reported the isolation of the complex diterpenoid maoecrystal V, from the leaves of the Chinese medicinal herb Isodon eriocalyx, whose structure was verified by x-ray crystallographic analysis. It possesses a unique architecture, with five highly congested rings and seven stereocenters, two of which are adjacent all carbon quaternary centers located in its interior. In addition to the complex structure of this natural product, it also has promising biological activity, showing selective cytotoxicity towards the HeLa tumor cell line at low concentration (IC50 =40 nM), and low toxicity towards other cell lines tested. For these reasons maoecrystal V has attracted significant attention from the synthetic community. Herein we report on many of the strategies that we have pursued towards the total synthesis. One of these strategies culminated in the stereoselective synthesis of the complete carbon skeleton of the natural product. The hallmarks of this strategy are the arylation of a substituted cyclohexane ring, followed by an oxidative dearomatization, and finally by an intramolecular Diels-Alder reaction in order to construct the [2.2.2]bicyclooctane moiety.


Efficiency in Natural Product Total Synthesis

Efficiency in Natural Product Total Synthesis
Author: Pei-Qiang Huang
Publisher: John Wiley & Sons
Total Pages: 512
Release: 2018-10-16
Genre: Science
ISBN: 1118605403

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Uniting the key organic topics of total synthesis and efficient synthetic methodologies, this book clearly overviews synthetic strategies and tactics applied in total synthesis, demonstrating how the total synthesis of natural products enables scientific and drug discovery. • Focuses on efficiency, a fundamental and important issue in natural products synthesis that makes natural product synthesis a powerful tool in biological and pharmaceutical science • Describes new methods like organocatalysis, multicomponent and cascade reactions, and biomimetic synthesis • Appeals to graduate students with two sections at the end of each chapter illustrating key reactions, strategies, tactics, and concepts; and good but unfinished total synthesis (synthesis of core structure) before the last section • Compiles examples of solid phase synthesis and continuing flow chemistry-based total synthesis which are very relevant and attractive to industry R&D professionals


Asymmetric Dearomatization Reactions

Asymmetric Dearomatization Reactions
Author: Shu-Li You
Publisher: John Wiley & Sons
Total Pages: 424
Release: 2016-06-03
Genre: Science
ISBN: 3527698485

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The first comprehensive account of the rapidly growing field of asymmetric dearomatization reactions with a focus on catalytic methods. It introduces the concept of dearomatization and describes recent progress in asymmetric reaction procedures with different catalyst systems, such as organocatalysts, transition metal catalysts, and enzymes. Chapters on dearomatizations of electron-deficient aromatic rings, dearomatization reactions via transition metal-catalyzed cross-couplings as well as dearomatization strategies in the synthesis of complex natural products are also included. Written by pioneers in the field, this is a highly valuable source of information not only for professional synthetic chemists in academia and industry but also for all those are interested in asymmetric methodologies and organic synthesis in general.


From Biosynthesis to Total Synthesis

From Biosynthesis to Total Synthesis
Author: Alexandros L. Zografos
Publisher: John Wiley & Sons
Total Pages: 585
Release: 2016-04-18
Genre: Science
ISBN: 1118751736

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Focusing on biosynthesis, this book provides readers with approaches and methodologies for modern organic synthesis. By discussing major biosynthetic pathways and their chemical reactions, transformations, and natural products applications; it links biosynthetic mechanisms and more efficient total synthesis. • Describes four major biosynthetic pathways (acetate, mevalonate, shikimic acid, and mixed pathways and alkaloids) and their related mechanisms • Covers reactions, tactics, and strategies for chemical transformations, linking biosynthetic processes and total synthesis • Includes strategies for optimal synthetic plans and introduces a modern molecular approach to natural product synthesis and applications • Acts as a key reference for industry and academic readers looking to advance knowledge in classical total synthesis, organic synthesis, and future directions in the field


Advances in Organometallic Chemistry

Advances in Organometallic Chemistry
Author:
Publisher: Academic Press
Total Pages: 300
Release: 2016-10-21
Genre: Science
ISBN: 0128050756

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Advances in Organometallic Chemistry contains authoritative review articles of worldwide known researchers on the field of organometallic chemistry, covering topics in organometallic synthesis, reactions, mechanisms, homogeneous catalysis, and more. The book will benefit a wide range of researchers involved in organometallic chemistry, including synthetic protocols, mechanistic studies, and practical applications. Contains contributions from leading authorities in the field of organometallic chemistry Covers topics in organometallic synthesis, reactions, mechanisms, homogeneous catalysis, and more Informs and updates readers on all the latest developments in the field Carefully edited to provide easy-to-read material