Synthesis of Lycodine-Type Lycopodium Alkaloids Using C-H Functionalization Tactics

Synthesis of Lycodine-Type Lycopodium Alkaloids Using C-H Functionalization Tactics PDF Author: James Newton
Publisher:
ISBN:
Category :
Languages : en
Pages : 97

Book Description
This dissertation describes our syntheses of several lycodine-type Lycopodium alkaloids by the late-stage C-H functionalization of lycodine derivatives. Lycodine-type alkaloids are well-known for their neurological activity. For example, huperzine A is a potent acetylcholinesterase inhibitor and the complanadine family of molecules has been shown to induce the secretion of Nerve Growth Factor. Due to these properties, lycodine-type alkaloids serve as interesting lead compounds for the development of new therapies for neurodegenerative disorders, such as Alzheimer's disease. Unsurprisingly, these molecules have attracted the attention of the synthetic community. Chapter 1 reviews syntheses of lycodine-type Lycopodium alkaloids with particular emphasis on the syntheses of biologically active congeners. Chapter 2 describes our synthesis of complanadine B, an unsymmetrical dimer of lycodine, using two approaches. In the first, the requisite skeletal oxygenation was installed early in the synthetic sequence. Our second approach utilized a blocking group strategy to enable the late-stage oxygenation of the complanadine skeleton by preventing oxygenation at undesired sites. Chapter 3 describes our efforts toward the synthesis of the casuarinine family of Lycopodium alkaloids by the late-stage C-H functionalization of lycodine derivatives. Using this strategy, we have been able to complete the synthesis of casuarinine D and have made significant progress toward the synthesis of casuarinine H, which we believe can serve as an intermediate in the synthesis of several other lycodine-type alkaloids.

Toward the Synthesis of the Magellaninone- and Lycopladine-type Lycopodium Alkaloids

Toward the Synthesis of the Magellaninone- and Lycopladine-type Lycopodium Alkaloids PDF Author: Rebecca Anne Murphy
Publisher:
ISBN:
Category :
Languages : en
Pages : 340

Book Description
This dissertation describes our strategy toward the synthesis of a variety of fawcettimine-type Lycopodium alkaloids. The first section focuses on the classification, structure, and historical significance of these natural products. This section also includes a proposal for their biosynthesis and a survey of the biological activities of the members of this class. The second section describes our work toward magellanine, magellaninone, and paniculatine. Two existing syntheses of these molecules are discussed, along with the strategy that we chose to employ in our work. We first pursue the synthesis of these natural products using a C4 pyridine C-H functionalization strategy that is based on precedent by the Fagnou and Echavarren groups. We then describe a C3 pyridine C-H functionalization approach that has more diverse methodological inspiration, although the original synthetic disconnection strategy derives from work done by the Jin Quan Yu group. Both of these synthetic endeavors are detailed herein. Finally, the third section covers our efforts toward the synthesis of lycopladines B, C, and D. We describe our "Heathcock-inspired"cascade approach toward the divergent synthesis of these three natural products. In this work, we have pursued the synthesis of a number of different substrates. We conclude with a summary of how this approach has evolved into a number of other projects within our group.

Alkaloid Synthesis

Alkaloid Synthesis PDF Author: Hans-Joachim Knölker
Publisher: Springer Science & Business Media
ISBN: 3642255299
Category : Science
Languages : en
Pages : 268

Book Description
Lycopodium Alkaloids: Isolation and Asymmetric Synthesis, by Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, by Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, by Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, by Yasuyuki Kita and Hiromichi Fujioka.- Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids, by Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, by Ingmar Bauer and Hans-Joachim Knölker.-

The logic of chemical synthesis

The logic of chemical synthesis PDF Author: E.J. Corey
Publisher: Рипол Классик
ISBN: 5885010811
Category : Science
Languages : en
Pages : 447

Book Description


Total Synthesis of Natural Products

Total Synthesis of Natural Products PDF Author: Jie Jack Li
Publisher: Springer Science & Business Media
ISBN: 3642340652
Category : Science
Languages : en
Pages : 292

Book Description
'Total Synthesis of Natural Products' is written and edited by some of today's leaders in organic chemistry. Eleven chapters cover a range of natural products, from steroids to alkaloids. Each chapter contains an introduction to the natural product in question, descriptions of its biological and pharmacological properties and outlines of total synthesis procedures already carried out. Particular emphasis is placed on novel methodologies developed by the respective authors and their research groups. This text is ideal for graduate and advanced undergraduate students, as well as organic chemists in academia and industry.

Alkaloid Synthesis

Alkaloid Synthesis PDF Author: Hans-Joachim Knoelker
Publisher: Springer Science & Business Media
ISBN: 3642255280
Category : Science
Languages : en
Pages : 268

Book Description
Lycopodium Alkaloids: Isolation and Asymmetric Synthesis, by Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, by Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, by Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, by Yasuyuki Kita and Hiromichi Fujioka.- Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids, by Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, by Ingmar Bauer and Hans-Joachim Knölker.-

Side Reactions in Organic Synthesis

Side Reactions in Organic Synthesis PDF Author: Florencio Zaragoza Dörwald
Publisher: John Wiley & Sons
ISBN: 3527604987
Category : Science
Languages : en
Pages : 389

Book Description
Most syntheses in the chemical research laboratory fail and usually require several attempts before proceeding satisfactorily. Failed syntheses are not only discouraging and frustrating, but also cost a lot of time and money. Many failures may, however, be avoided by understanding the structure-reactivity relationship of organic compounds. This textbook highlights the competing processes and limitations of the most important reactions used in organic synthesis. By allowing chemists to quickly recognize potential problems this book will help to improve their efficiency and success-rate. A must for every graduate student but also for every chemist in industry and academia. Contents: 1 Organic Synthesis: General Remarks 2 Stereoelectronic Effects and Reactivity 3 The Stability of Organic Compounds 4 Aliphatic Nucleophilic Substitutions: Problematic Electrophiles 5 The Alkylation of Carbanions 6 The Alkylation of Heteroatoms 7 The Acylation of Heteroatoms 8 Palladium-Catalyzed C-C Bond Formation 9 Cyclizations 10 Monofunctionalization of Symmetric Difunctional Substrates

Innovations in Chemical Biology

Innovations in Chemical Biology PDF Author: Bilge Sener
Publisher: Springer Science & Business Media
ISBN: 1402069553
Category : Science
Languages : en
Pages : 428

Book Description
This book includes 49 chapters presented as plenary , invited lectures and posters at the conference. Six plenary lectures have published in an issue of Pure and Applied Chemistry, Vol. 79, No. 12, 2007; the titles of these presentations are given as an Annex at the end of the book. I thank all contrib utors for the preparation of their presentations. It is sad to report that Professor Hitoshi Ohtaki, one of the founders of the Eurasia conferences and contributors passed away on November 5, 2006. Professor Ohtaki enthusiastically promoted international cooperation and took it upon himself to p- licize Japanese science to the wider world. His contribution in this book will serve as a memorable contribution to that goal. He will be missed by all of us. This book is dedicated to his memory. Professor Dr . Bilge S ̧ ener Editor Memorial Tribute to Professor Dr. Hitoshi Ohtaki Curriculum Vitae of Hitoshi Ohtaki Date of Birth September 16, 1932 Place of Birth T ok yo, Japan Date of Decease November 5, 2006 (at the age of 74) Addr ess 3-9-406 Namiki-2-chome, Kanazawa-ku, Yokohama, Japan Institution Chair Professor of The Research Organization of Science and Engineering, Ritsumeikan University Guest Professor of Yokohama City University Education Bachelor of Science, Nagoya University, 1955 Master of Science, Nagoya University, 1957 Doctor of Science, Nagoya University, 1961 ix x Memorial Tribute to Professor Dr.

Cobalt Catalysis in Organic Synthesis

Cobalt Catalysis in Organic Synthesis PDF Author: Marko Hapke
Publisher: John Wiley & Sons
ISBN: 3527344500
Category : Technology & Engineering
Languages : en
Pages : 480

Book Description
Provides a much-needed account of the formidable "cobalt rush" in organic synthesis and catalysis Over the past few decades, cobalt has turned into one of the most promising metals for use in catalytic reactions, with important applications in the efficient and selective synthesis of natural products, pharmaceuticals, and new materials. Cobalt Catalysis in Organic Synthesis: Methods and Reactions provides a unique overview of cobalt-catalysed and -mediated reactions applied in modern organic synthesis. It covers a broad range of homogeneous reactions, like cobalt-catalysed hydrogenation, hydrofunctionalization, cycloaddition reactions, C-H functionalization, as well as radical and biomimetic reactions. First comprehensive book on this rapidly evolving research area Covers a broad range of homogeneous reactions, such as C-H activation, cross-coupling, synthesis of heterocyclic compounds (Pauson-Khand), and more Chapters on low-valent cobalt complexes as catalysts in coupling reactions, and enantioselective cobalt-catalyzed transformations are also included Can be used as a supplementary reader in courses of advanced organic synthesis and organometallic chemistry Cobalt Catalysis in Organic Synthesis is an ideal book for graduates and researchers in academia and industry working in the field of synthetic organic chemistry, catalysis, organometallic chemistry, and natural product synthesis.

Efficiency in Natural Product Total Synthesis

Efficiency in Natural Product Total Synthesis PDF Author: Pei-Qiang Huang
Publisher: John Wiley & Sons
ISBN: 1118940210
Category : Science
Languages : en
Pages : 512

Book Description
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