Gallium(III)-Catalyzed Cycloisomerization Approach Toward C20-Diterpenoid Alkaloids

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ISBN 13 :
Total Pages : 164 pages
Book Rating : 4.:/5 (94 download)

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Book Synopsis Gallium(III)-Catalyzed Cycloisomerization Approach Toward C20-Diterpenoid Alkaloids by : Amy Michelle Hamlin

Download or read book Gallium(III)-Catalyzed Cycloisomerization Approach Toward C20-Diterpenoid Alkaloids written by Amy Michelle Hamlin and published by . This book was released on 2014 with total page 164 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation discusses our gallium(III)-catalyzed cycloisomerization approach toward the hetidine and hetisine-type diterpenoid alkaloids. The first chapter presents the background of the gallium(III)-catalyzed cycloisomerization reaction. The initial reports for the skeletal rearrangements of 1,6-enyned will be presented and the expansion of the substrate scope to include indenyl alkynes to provide cycloheptadiene products will be discussed. The chapter will conclude with the application of the indenyl alkyne cycloisomerization reaction to the synthesis of several icetexane diterpenoids. The second chapter focuses on the structure and classification of the C20- diterpenoid alkaloids. The biological activity of selected alkaloids will be discussed. Several approached toward the hetidine and hetisine cores will also be presented along with the two completed total syntheses of the hetisine-type diterpenoid alkaloid nominine. Chapter three presents our approach toward the hetidine core using the gallium(III)- catalyzed cycloisomerization strategy. Our retrosynthetic analysis of a key-intermediate resembling the hetidine core, that we proposed could be used to access both hetidine and hetisine-type natural products, will be discussed. Synthesis of the cycloisomerization substrate will be presented along with the elaboration of the resulting cycloheptadiene to an intermediate similar to that used by Gin and Peese in their synthesis of nominine. Finally, an oxidative dearomatization approach toward the [2.2.2] bicycle and completion of the hetidine core will be presented. The final chapter discusses the elaboration of the hetidine core to dihydronavirine A in an attempt to access the hetidine-type natural product navirine A. An interesting C-C bond cleaving reaction, which provides the atisine core from the hetidine core, was also explored.

Ga(III)-Catalyzed Cycloisomerization Approach to the Icetexones and Nominine

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ISBN 13 :
Total Pages : 338 pages
Book Rating : 4.:/5 (858 download)

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Book Synopsis Ga(III)-Catalyzed Cycloisomerization Approach to the Icetexones and Nominine by : Felipe de Jesus Cortez

Download or read book Ga(III)-Catalyzed Cycloisomerization Approach to the Icetexones and Nominine written by Felipe de Jesus Cortez and published by . This book was released on 2011 with total page 338 pages. Available in PDF, EPUB and Kindle. Book excerpt: The icetexane diterpenoids is a group of natural products isolated from various members of the Salvia genus. These compounds contain a [6-7-6] tricyclic motif and vary by the level of oxidation on the seven-membered ring and oxygenation of the arene moiety. The synthesis of these compounds has been achieved by our group through the use of a Ga(III)-catalyzed cycloisomerization of indenyl alkynes. This thesis explores the synthesis of the icetexone subclass of diterpenoids, which contain extra functionalization, using a similar cycloisomerization strategy. The synthesis of icetexone was first attempted through the use of a remote functionalization strategy to form the desired lactone. However, all attempts were unsuccessful. Therefore, a second generation approach using a pre-functionalized indenyl alkyne in the Ga(III)-cycloisomerization reaction yielded the desired tricyclic intermediate. A tandem epoxide opening, lactone formation, and reductive transposition sequence completed the formal synthesis of both icetexone and 5-epi-icetexone. Progress toward anastomosine, another member in this subclass, was also made. Another family of compounds that was targeted using the Ga(III)- catalyzed cycloisomerization is the C20 diterpenoid alkaloids. This large family of natural products is found in traditional Eastern medicines and has unique and complex structures. The hetisine type of natural products is characterized by their rigid heptacyclic core and a bicyclo[2.2.2]octane motif. We believed that our Ga(III) cycloisomerization methodology would enable access to the [6-7-6] tricyclic core of these molecules as a starting point for their successful synthesis. The synthesis of nominine was first attempted through an acid catalyzed hydroamination of a cycloheptadiene accessed from the Ga(III)-cycloisomerization. Low yields of the hydroamination as well as later transformations led us to develop a second- generation strategy that involved dihydroxylation of the cycloheptadiene and monoprotection of a resulting diol. Both routes are currently being explored to complete the synthesis of nominine.

Mechanochemical Organic Synthesis

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Publisher : Elsevier
ISBN 13 : 0128025255
Total Pages : 388 pages
Book Rating : 4.1/5 (28 download)

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Book Synopsis Mechanochemical Organic Synthesis by : Davor Margetic

Download or read book Mechanochemical Organic Synthesis written by Davor Margetic and published by Elsevier. This book was released on 2016-04-23 with total page 388 pages. Available in PDF, EPUB and Kindle. Book excerpt: Mechanochemical Organic Synthesis is a comprehensive reference that not only synthesizes the current literature but also offers practical protocols that industrial and academic scientists can immediately put to use in their daily work. Increasing interest in green chemistry has led to the development of numerous environmentally-friendly methodologies for the synthesis of organic molecules of interest. Amongst the green methodologies drawing attention, mechanochemistry is emerging as a promising method to circumvent the use of toxic solvents and reagents as well as to increase energy efficiency. The development of synthetic strategies that require less, or the minimal, amount of energy to carry out a specific reaction with optimum productivity is of vital importance for large-scale industrial production. Experimental procedures at room temperature are the mildest reaction conditions (essentially required for many temperature-sensitive organic substrates as a key step in multi-step sequence reactions) and are the core of mechanochemical organic synthesis. This green synthetic method is now emerging in a very progressive manner and until now, there is no book that reviews the recent developments in this area. - Features cutting-edge research in the field of mechanochemical organic synthesis for more sustainable reactions - Integrates advances in green chemistry research into industrial applications and process development - Focuses on designing techniques in organic synthesis directed toward mild reaction conditions - Includes global coverage of mechanochemical synthetic protocols for the generation of organic compounds

Methods and Applications of Cycloaddition Reactions in Organic Syntheses

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Publisher : John Wiley & Sons
ISBN 13 : 1118778200
Total Pages : 996 pages
Book Rating : 4.1/5 (187 download)

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Book Synopsis Methods and Applications of Cycloaddition Reactions in Organic Syntheses by : Nagatoshi Nishiwaki

Download or read book Methods and Applications of Cycloaddition Reactions in Organic Syntheses written by Nagatoshi Nishiwaki and published by John Wiley & Sons. This book was released on 2013-12-17 with total page 996 pages. Available in PDF, EPUB and Kindle. Book excerpt: Advanced tools for developing new functional materials and applications in chemical research, pharmaceuticals, and materials science Cycloadditions are among the most useful tools for organic chemists, enabling them to build carbocyclic and heterocyclic structures. These structures can then be used to develop a broad range of functional materials, including pharmaceuticals, agrochemicals, dyes, and optics. With contributions from an international team of leading experts and pioneers in cycloaddition chemistry, this book brings together and reviews recent advances, trends, and emerging research in the field. Methods and Applications of Cycloaddition Reactions in Organic Syntheses focuses on two component cycloadditions, with chapters covering such topics as: N1 unit transfer reaction to C–C double bonds [3+2] Cycloaddition of α, β-unsaturated metal-carbene complexes Formal [3+3] cycloaddition approach to natural product synthesis Development of new methods for the construction of heterocycles based on cycloaddition reaction of 1,3-dipoles Cycloreversion approach for preparation of large π-conjugated compounds Transition metal-catalyzed or mediated [5+1] cycloadditions Readers will learn methods for seamlessly executing important reactions such as Diels-Alder and stereoselective dipolar reactions in order to fabricate heterocyclic compounds, natural products, and functional molecules. The book not only features cutting-edge topics, but also important background information, such as the contributors’ process for developing new methodologies, to help novices become fully adept in the field. References at the end of each chapter lead to original research papers and reviews for facilitating further investigation of individual topics. Covering the state of the science and technology, Methods and Applications of Cycloaddition Reactions in Organic Syntheses enables synthetic organic chemists to advance their research and develop new functional materials and applications in chemical research, pharmaceuticals, and materials science.

Total Synthesis of Natural Products

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Publisher : Springer Science & Business Media
ISBN 13 : 3642340652
Total Pages : 292 pages
Book Rating : 4.6/5 (423 download)

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Book Synopsis Total Synthesis of Natural Products by : Jie Jack Li

Download or read book Total Synthesis of Natural Products written by Jie Jack Li and published by Springer Science & Business Media. This book was released on 2013-03-14 with total page 292 pages. Available in PDF, EPUB and Kindle. Book excerpt: '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.

Efficiency in Natural Product Total Synthesis

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Publisher : John Wiley & Sons
ISBN 13 : 1118940210
Total Pages : 512 pages
Book Rating : 4.1/5 (189 download)

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Book Synopsis Efficiency in Natural Product Total Synthesis by : Pei-Qiang Huang

Download or read book Efficiency in Natural Product Total Synthesis written by Pei-Qiang Huang and published by John Wiley & Sons. This book was released on 2018-07-24 with total page 512 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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

Name Reactions for Carbocyclic Ring Formations

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Publisher : John Wiley & Sons
ISBN 13 : 0470872209
Total Pages : 774 pages
Book Rating : 4.4/5 (78 download)

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Book Synopsis Name Reactions for Carbocyclic Ring Formations by : Jie Jack Li

Download or read book Name Reactions for Carbocyclic Ring Formations written by Jie Jack Li and published by John Wiley & Sons. This book was released on 2010-10-12 with total page 774 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book continues the well-established and authoritative series on name reactions in organic chemistry by focusing on name reactions on ring formation. Ring formating reactions have found widespread applicability in traditional organic synthesis, medicinal/pharmaceuticals, agricultural, fine chemicals, and of late, especially in polymer science.

Protecting-Group-Free Organic Synthesis

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Publisher : John Wiley & Sons
ISBN 13 : 1119295203
Total Pages : 283 pages
Book Rating : 4.1/5 (192 download)

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Book Synopsis Protecting-Group-Free Organic Synthesis by : Rodney A. Fernandes

Download or read book Protecting-Group-Free Organic Synthesis written by Rodney A. Fernandes and published by John Wiley & Sons. This book was released on 2018-08-20 with total page 283 pages. Available in PDF, EPUB and Kindle. Book excerpt: Presents a comprehensive account of established protecting-group-free synthetic routes to molecules of medium to high complexity This book supports synthetic chemists in the design of strategies, which avoid or minimize the use of protecting groups so as to come closer to achieving an “ideal synthesis” and back the global need of practicing green chemistry. The only resource of its kind to focus entirely on protecting-group-free synthesis, it is edited by a leading practitioner in the field, and features enlightening contributions by top experts and researchers from across the globe. The introductory chapter includes a concise review of historical developments, and discusses the concepts, need for, and future prospects of protecting-group-free synthesis. Following this, the book presents information on protecting-group-free synthesis of complex natural products and analogues, heterocycles, drugs, and related pharmaceuticals. Later chapters discuss practicing protecting-group-free synthesis using carbohydrates and of glycosyl derivatives, glycol-polymers and glyco-conjugates. The book concludes with a chapter on latent functionality as a tactic toward formal protecting-group-free synthesis. A comprehensive account of established protecting-group-free (PGF) synthetic routes to molecules of medium to high complexity Benefits total synthesis, methodology development and drug synthesis researchers Supports synthetic chemists in the design of strategies, which avoid or minimize the use of protecting groups so as to come closer to achieving an “ideal synthesis” and support the global need of practicing green chemistry Covers a topic that is gaining importance because it renders syntheses more economical Protecting-Group-Free Organic Synthesis: Improving Economy and Efficiency is an important book for academic researchers in synthetic organic chemistry, green chemistry, medicinal and pharmaceutical chemistry, biochemistry, and drug discovery.

Natural Products Chemistry

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Publisher :
ISBN 13 : 9780198557111
Total Pages : 0 pages
Book Rating : 4.5/5 (571 download)

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Book Synopsis Natural Products Chemistry by : Koji Nakanishi

Download or read book Natural Products Chemistry written by Koji Nakanishi and published by . This book was released on 1974 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Comprehensive Organometallic Chemistry III, Volume 3

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ISBN 13 :
Total Pages : 976 pages
Book Rating : 4.F/5 ( download)

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Book Synopsis Comprehensive Organometallic Chemistry III, Volume 3 by : D. M. P. Mingos

Download or read book Comprehensive Organometallic Chemistry III, Volume 3 written by D. M. P. Mingos and published by . This book was released on 2007 with total page 976 pages. Available in PDF, EPUB and Kindle. Book excerpt: Provides essential information for any chemist or technologist who needs to use or apply organometallic compounds. Provides a comprehensive overview of recent developments in the field and attempts to predict trends in the field over the next ten years.

Superelectrophiles and Their Chemistry

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Publisher : John Wiley & Sons
ISBN 13 : 0470185112
Total Pages : 312 pages
Book Rating : 4.4/5 (71 download)

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Book Synopsis Superelectrophiles and Their Chemistry by : George A. Olah

Download or read book Superelectrophiles and Their Chemistry written by George A. Olah and published by John Wiley & Sons. This book was released on 2008-01-03 with total page 312 pages. Available in PDF, EPUB and Kindle. Book excerpt: Superelectrophiles and Their Chemistry contains, for the first-time, a discussion of the basics of this emerging field of organic chemistry, alongside tools to help the reader apply the chemistry. Specific tools include an evaluation of the ways to increase the strength of electrophiles, the classification of superelectrophiles, the solvation issues, a review of methods for studying superelectrophilicity, with details of the superelectrophiles that have been identified and studied. Additional information includes substituent effects in activation of superelectrophiles, and solvation in chemical reactions, as well as an insightful look into future applications.

Challenges in Synthetic Organic Chemistry

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Publisher : Oxford University Press, USA
ISBN 13 :
Total Pages : 248 pages
Book Rating : 4.:/5 (318 download)

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Book Synopsis Challenges in Synthetic Organic Chemistry by : Teruaki Mukaiyama

Download or read book Challenges in Synthetic Organic Chemistry written by Teruaki Mukaiyama and published by Oxford University Press, USA. This book was released on 1994 with total page 248 pages. Available in PDF, EPUB and Kindle. Book excerpt: This volume describes the life's work of Professor Teruaki Mukaiyama, one of Japan's most important and respected synthetic organic chemists. It includes information on his early research into a wide range of reactions, including dehydration reactions, the use of organosulfur compounds, and oxidation-reduction condensations in peptide and nucleotide synthesis reagents, as well as an account of Mukaiyama's important work on the applications of titanium compounds in organic synthesis. Three final chapters review Mukaiyama's work in synthetic control, stereoselective synthesis of carbohydrates, the stereoselective aldol, and Michael reactions. This unique book makes accessible much research that has only been available in Japanese, and provides a rare account of the contributions of one of the world's leading chemists.