New Gold-Catalyzed Reactions and Applications for the Synthesis of Alkaloids PDF Download

Author: Ana Escribano Cuesta
Publisher: Springer Science & Business Media
ISBN: 3319007025
Category : Science
Languages : en
Pages : 202

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Book Description
Ana Escribano Cuesta's thesis presents a detailed study of the inter- and intramolecular reactions of carbonyl compounds with 1,6-enynes using gold (I) complexes. An important part of the work involved streamlining the variables that allow the selective synthesis of different products such as tricyclic compounds, dihydropyrans, 1,3-dienes or cyclobutenes. The second chapter highlights the importance and difficulties in synthesising a cyclobutene subunit and the author includes a detailed description of how the products were prepared. The final chapter outlines the synthesis of lundurines using methodology developed by the author's research group for intramolecular gold-catalyzed cyclization of indoles with alkynes. The lundurine products developed in this work show significant in vitro cytoxicity toward B16 melanoma cells. The work in this thesis has led to a number of publications in high-profile chemistry journals.

Author: Pei-Qiang Huang
Publisher: John Wiley & Sons
ISBN: 1118605403
Category : Science
Languages : en
Pages : 512

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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

Author: Xiao-Yu Sun
Publisher: Springer Science & Business Media
ISBN: 3642271952
Category : Science
Languages : en
Pages : 232

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Book Description
In his thesis, Xiaoyu Sun conducts the first total synthesis of all possible stereoisomers of plakortide E and also confirms the absolute configuration of natural plakortide E. Xiaoyu Sun subsequently converts Plakortide E methyl ester to plakortone B in a biomimetic conversion. Construction and functionalization of cyclic peroxides are notoriously difficult due to the very low O-O bond dissociation energy. Plaktoride E is isolated from the Jamaican marine sponge platorits halichondrioides and contains a five-membered peroxide ring, with oxygen atoms linked to tertiary C4 and C6 centers. The methodology used for synthesizing highly substituted cyclic peroxides is novel and useful, and not only extends the field of Pd-catalyzed reactions, but also provides a convenient synthetic approach for the preparation of the 1,2-dioxolanes series. Plakortide E and plakortone B are bioactive, which means that the synthetic studies on them and their analogs are pivotal in drug discovery.

Author: Marco Bandini
Publisher: Springer
ISBN: 3319351443
Category : Science
Languages : en
Pages : 294

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Book Description
The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field. All chapters from Topics in Heterocyclic Chemistry are published Online First with an individual DOI. In references, Topics in Heterocyclic Chemistry is abbreviated as Top Heterocycl Chem and cited as a journal

Author: Shuanhu Gao
Publisher: Thieme
ISBN: 3131999012
Category : Science
Languages : en
Pages : 818

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Book Description
Significant advances in metal-catalyzed reactions, especially cyclizations, have dramatically improved the efficiency of organic synthesis over the last three decades. To date these transformations are widely used in the area of synthesis of both natural products and therapeutic agents. "Science of Synthesis: Metal-Catalyzed Cyclization Reactions" presents the most commonly used and significant metal-catalyzed reactions for modern organic synthesis. The basic principles, the current state of the art, scope, limitations, and mechanism of these reactions are also discussed. Typical examples of target synthesis are provided to help inspire further applications. Volume 1 covers intramolecular coupling reactions (including Heck reactions), intramolecular allylations, and cyclopropane and cyclopropene ring openings. Also included are cyclization reactions of alkenes, alkynes, and allenes, cycloisomerizations, and intramolecular C-N and C-O bond formation.

Author: Shengming Ma
Publisher: Thieme
ISBN: 3131998512
Category : Science
Languages : en
Pages : 1198

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Book Description
Significant advances in metal-catalyzed reactions, especially cyclizations, have dramatically improved the efficiency of organic synthesis over the last three decades. To date these transformations are widely used in the area of synthesis of both natural products and therapeutic agents. "Science of Synthesis: Metal-Catalyzed Cyclization Reactions" presents the most commonly used and significant metal-catalyzed reactions for modern organic synthesis. The basic principles, the current state of the art, scope, limitations, and mechanism of these reactions are also discussed. Typical examples of target synthesis are provided to help inspire further applications. Volume 2 covers epoxidations, aziridinations, cyclopropanations, and Pauson-Khand reactions, as well as a wide range of cycloaddition processes, radical cyclizations, and ring-closing metathesis.

Author: Vittorio Caprio
Publisher: John Wiley & Sons
ISBN: 1405190914
Category : Science
Languages : en
Pages : 409

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Book Description
Asymmetric synthesis has become a major aspect of modern organic chemistry. The stereochemical properties of an organic compound are often essential to its bioactivity, and the need for stereochemically pure pharmaceutical products is a key example of the importance of stereochemical control in organic synthesis. However, achieving high levels of stereoselectivity in the synthesis of complex natural products represents a considerable intellectual and practical challenge for chemists. Written from a synthetic organic chemistry perspective, this text provides a practical overview of the field, illustrating a wide range of transformations that can be achieved. The book captures the latest advances in asymmetric catalysis with emphasis placed on non-enzymatic methods. Topics covered include: Reduction of alkenes, ketones and imines Nucleophilic addition to carbonyl compounds Catalytic carbon-carbon bond forming reactions Catalytic reactions involving metal carbenoids Conjugate addition reactions Catalysis in Asymmetric Synthesis bridges the gap between undergraduate and advanced level textbooks and provides a convenient point of entry to the primary literature for the experienced synthetic organic chemist.

Author: Qiao Yan
Publisher:
ISBN:
Category :
Languages : en
Pages : 0

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Book Description
The body of this thesis is comprised of four scientific articles and is preceded by an overview that contextualises all of this submitted/published work. The first major part of this thesis is comprised of Publication 1. This details work concerned with establishing the true structure of the sorbicillinoid-derived isolate rezishanone C by total synthesis. Specifically, the enantiomer of what proved to be the true structure of the sorbicillinoid rezishanone C (sorbivinetone) was synthesized from the homochiral cis-1,2-dihydrocatechol that is itself generated through the whole-cell biotransformation of toluene. These studies and dispersion-corrected DFT calculations support the proposal that rezishanone C is an artefact of the isolation process and arises through a Diels-Alder cycloaddition reaction between ethyl vinyl ether and sorbicillinol. The second major part of the thesis is comprised of Publication 2. This is concerned with the synthesis and photochemical rearrangements of enantiomerically pure, polysubstituted and, in some cases, variously annulated bicyclo[2.2.2]octenones. Specifically, then, a series of bicyclo[2.2.2]octenones has been prepared by engaging the enzymatically-derived and enantiomerically pure cis-1,2-dihydrocatechol in either inter- or intra-molecular Diels-Alder cycloaddition reactions with various dienophiles. These polycyclic adducts or simple derivatives thereof were shown to readily participate in both photochemically promoted 1,3-acyl migration and oxa-di-pi-methane rearrangement processes to give corresponding products. The third major part of the thesis is comprised of Publication 3. This details the establishment of a palladium-catalyzed Ullmann cross-coupling/reductive cyclization route to the carbazole natural products 3-methyl-9H-carbazole, glycoborine, glycozoline, clausazoline K, mukonine and karapinchamine A. These were prepared by reductive cyclisation of the relevant 2-arylcyclohex-2-en-1-one to the corresponding tetrahydrocarbazole and dehydrogenation of this to give the target carbazole. Compounds of 2-arylcyclohex-2-en-1-one were themselves prepared using a palladium-catalyzed Ullmann cross-coupling reaction that served to link the appropriate 2-iodocyclohex-2-en-1-one and o-halonitrobenzene. The fourth and final part of the thesis is comprised of Publication 4. This details a unified approach to the isomeric alpha-, beta-, gamma- and delta-carbolines via their 6,7,8,9-tetrahydro counterparts. Specifically, then, a cross-coupling/reductive cyclisation protocol has been employed in preparing all four carbolines. So, for example, the 2-nitropyridine derivative, which is readily generated through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-alpha-carboline that is itself readily aromatized to give alpha-carboline.

Author: Michelangelo Gruttadauria
Publisher: John Wiley & Sons
ISBN: 0470641363
Category : Science
Languages : en
Pages : 720

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Book Description
This book covers advances in the methods of catalytic asymmetric synthesis and their applications. Coverage moves from new materials and technologies to homogeneous metal-free catalysts and homogeneous metal catalysts. The applications of several methodologies for the synthesis of biologically active molecules are discussed. Part I addresses recent advances in new materials and technologies such as supported catalysts, supports, self-supported catalysts, chiral ionic liquids, supercritical fluids, flow reactors and microwaves related to asymmetric catalysis. Part II covers advances and milestones in organocatalytic, enzymatic and metal-based mediated asymmetric synthesis, including applications for the synthesis of biologically active molecules. Written by leading international experts, this book consists of 16 chapters with 2000 References and illustrations of 560 schemes and figures.