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Enantiospecific Total Synthesis Of Welwitindolinone Alkaloids
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Book Synopsis Enantiospecific Total Synthesis of Welwitindolinone Alkaloids by : Evan Daniel Styduhar
Download or read book Enantiospecific Total Synthesis of Welwitindolinone Alkaloids written by Evan Daniel Styduhar and published by . This book was released on 2015 with total page 222 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter one provides a summary of efforts towards the syntheses of the welwitindolinones with bicyclo[4.3.1]decane cores. Emphasis is given to more recent approaches that have successfully assembled the bicyclic core of the natural products. Chapters two, three, and four present our total syntheses of the welwitindolinone natural products. The enantiospecific total syntheses of N-methylwelwitindolinone C isothiocyanate, N-methylwelwitindolinone D isonitrile, and N-methylwelwitindolinone B isothiocyanate are detailed. The approach to these natural products features an aryne cyclization to construct the bicyclo[4.3.1]decane core of the molecules as well as a C-H nitrene insertion reaction to install the bridgehead nitrogen substituent. In chapter three, a dual C-H functionalization event installs the challenging ether linkage and allows for completion of ( - )-N-methylwelwitindolinone D isonitrile. Chapter four details a regio- and diastereoselective chlorinative oxabicyclic opening to enable the first total synthesis of N-methylwelwitindolinone B isothiocyanate.
Book Synopsis Total Synthesis of Welwitindolinones and Nickel-Catalyzed Reactions of Amide Derivatives by : Nicholas Anthony Weires
Download or read book Total Synthesis of Welwitindolinones and Nickel-Catalyzed Reactions of Amide Derivatives written by Nicholas Anthony Weires and published by . This book was released on 2017 with total page 560 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation describes our efforts toward the total synthesis of welwitindolinone natural products, as well as the development of reactions involving the nickel-catalyzed activation of amide C-N bonds. The welwitindolinones have been long-standing targets in total synthesis for over two decades, and this dissertation describes two completed total syntheses of these alkaloids. In addition, several nickel-catalyzed transformations of amides are outlined, each of which demonstrate the powerful reactivity of nickel and highlight the utility of amides as synthetic building blocks. Chapters one and two present our enantiospecific total syntheses of the welwitindolinone alkaloids N-methylwelwitindolinone D isonitrile and N-methylwelwitindolinone B isothiocyanate. Our approach to these natural products features an aryne cyclization to construct the bicyclo[4.3.1]decane core of the molecules, as well as a C-H nitrene insertion reaction to introduce the bridgehead nitrogen substituent. In chapter one, a dual C-H functionalization event installs the challenging ether linkage and allows for completion of (-)-N-methylwelwitindolinone D isonitrile. In chapter two, a regio- and diastereoselective chlorinative oxabicyclic opening is detailed, which enables the first total synthesis of N-methylwelwitindolinone B isothiocyanate. Chapters three, four, and five describe the development of nickel-catalyzed carbon-carbon bond-forming reactions of amides. More specifically, chapters three and four outline the Suzuki-Miyaura couplings of aromatic and aliphatic amides, respectively, whereas chapter five details the alkylation of amide derivatives. These methodologies represent mild and complementary tools to the Weinreb ketone synthesis, proceeding through the nickel-catalyzed activation of the amide C-N bond. It is shown that amides, which were traditionally thought of as inert functionalities, can be utilized as synthons in C-C bond-forming reactions. Chapter six describes a method for the benchtop delivery of Ni(cod)2 involving the encapsulation of Ni(cod)2 in paraffin wax. Due to air- and moisture-sensitivity, Ni(cod)2 is normally handled under an inert atmosphere. Using our method of wax encapsulation, several nickel-catalyzed transformations are performed without the use of a glove box, including various amide C-N bond cleavage reactions. These studies are aimed at promoting the widespread use of nickel in transition metal catalysis. Chapter seven illustrates the kinetic modeling of the nickel-catalyzed esterification of amides. By developing a kinetic model, an optimization is undertaken that allows for the employment of catalyst loadings as low as 0.4 mol% nickel. This demonstration is intended to foster the advancement of kinetic modeling as a powerful tool in methodology development.
Book Synopsis Progress Toward a Total Synthesis of the Welwitindolinone Alkaloids by : Matthew Mark Weiss
Download or read book Progress Toward a Total Synthesis of the Welwitindolinone Alkaloids written by Matthew Mark Weiss and published by . This book was released on 2001 with total page 1242 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Enantiospecific Total Synthesis of (+)-vellosimine, (+)-normacusine B and ( - )-norsuaveoline as Well as an Improved Enantiospecific Total Synthesis of (+)-ajmaline and (+)-alkaloid G by : Tao Wang
Download or read book Enantiospecific Total Synthesis of (+)-vellosimine, (+)-normacusine B and ( - )-norsuaveoline as Well as an Improved Enantiospecific Total Synthesis of (+)-ajmaline and (+)-alkaloid G written by Tao Wang and published by . This book was released on 2001 with total page 608 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Synthetic Applications of the Type 2 Intramolecular Diels-Alder Reaction by : John A. Brailsford
Download or read book Synthetic Applications of the Type 2 Intramolecular Diels-Alder Reaction written by John A. Brailsford and published by . This book was released on 2009 with total page 278 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation describes the synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization cascade reaction. This cascade reaction prepares a highly functionalized welwitindolinone core structure containing two all-carbon quaternary centers, sets two stereocenters, and assembles all but two carbon atoms of the B and C welwitindolinone skeleton from simple materials in short fashion. Additionally, a novel route for the preparation of 4-vinyl oxindoles via the Suzuki cross-coupling reaction is described. In another project, asymmetric variants of the type 2 intramolecular Diels-Alder reaction incorporating oxazolidinone chiral auxiliaries were evaluated. This study has resulted in systems that deliver bridged bicyclic [5.3.1] and [4.3.1] ring systems in high diastereomeric (97-99% de)(and enantiomeric) purity.
Book Synopsis Enantiospecific Total Synthesis of the Indole Alkaloids Talpinine, Talcarpine, Alstonerine and Anhydromacrosalhine-methine as Well as Studies Directed Toward the Synthesis of the Oxindole Alkaloid Alstonisine by : Peng Yu
Download or read book Enantiospecific Total Synthesis of the Indole Alkaloids Talpinine, Talcarpine, Alstonerine and Anhydromacrosalhine-methine as Well as Studies Directed Toward the Synthesis of the Oxindole Alkaloid Alstonisine written by Peng Yu and published by . This book was released on 1999 with total page 606 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Total Synthesis of N-methylwelwitindolinone D Isonitrile by : Vikram Bhat
Download or read book Total Synthesis of N-methylwelwitindolinone D Isonitrile written by Vikram Bhat and published by . This book was released on 2011 with total page 250 pages. Available in PDF, EPUB and Kindle. Book excerpt: Synthesis of the characteristic bridged-bicylic skeleton of the welwitindolinone alkaloids was achieved via manganese(III) promoted oxidative cyclization and palladium catalyzed enolate arylation reactions. Total synthesis of N-methylwelwitindolinone D isonitrile was accomplished. Synthesis of 20,21-dihydro N-methylwelwitindolinone B isothiocyanate was also completed. During the course of these synthetic efforts, several interesting and unexpected observations were made.
Book Synopsis General Approach for the Synthesis of Macroline/sarpagine Alkaloids by : Yingzhi Bi
Download or read book General Approach for the Synthesis of Macroline/sarpagine Alkaloids written by Yingzhi Bi and published by . This book was released on 1994 with total page 376 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Total Synthesis of Welwitindolinone Natural Products by : Alexander David Huters
Download or read book Total Synthesis of Welwitindolinone Natural Products written by Alexander David Huters and published by . This book was released on 2013 with total page 254 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter one provides a summary of efforts towards the syntheses of the welwitindolinones with bicyclo[4.3.1]decane cores. Emphasis is given to more recent approaches that have successfully assembled the bicyclic core of the natural products. Chapters two and three are a discussion of our studies relating to a model system of the welwitindolinone natural products. Chapter two focuses on the use of an aryne cyclization to assemble the bicyclo[4.3.1]decane framework of the welwitindolinones. Chapter three covers initial attempts to install the bridgehead nitrogen substituent present in the natural products in addition to the synthesis of a functionalized aryne cyclization substrate. Chapters four and five present our total syntheses of the welwitindolinone natural products. The enantiospecific total syntheses of N-methylwelwitindolinone C isothiocyanate, N-methylwelwitindolinone C isonitrile, 3-hydroxy-N-methylwelwitindolinone C isothiocyanate and 3-hydroxy-N-methylwelwitindolinone C isonitrile are detailed. The approach to these natural products features an aryne cyclization to construct the bicyclo[4.3.1]decane core of the molecules as well as a late-stage nitrene insertion reaction to install the bridgehead nitrogen substituent. The use of a deuterium kinetic isotope effect to improve the yield of the nitrene insertion is also presented. In addition, a computational method to predict the stereochemistry of a previously unconfirmed stereocenter in the hydroxylated natural products as well as experimental validation of the computational findings is discussed.
Book Synopsis The Enantiospecific Stereospecific Total Synthesis of the Enantiomers of the Indole Alkaloids Na-methylvellosimine, Affinisine and Macroline as Well as the Total Synthesis of the Indole Alkaloids Trinervine, Alstophylline and the Antimalarial Bisindole Macralstonine by : Xiaoxiang Liu
Download or read book The Enantiospecific Stereospecific Total Synthesis of the Enantiomers of the Indole Alkaloids Na-methylvellosimine, Affinisine and Macroline as Well as the Total Synthesis of the Indole Alkaloids Trinervine, Alstophylline and the Antimalarial Bisindole Macralstonine written by Xiaoxiang Liu and published by . This book was released on 2002 with total page 642 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Part I. The Enantiospecific Total Synthesis of Tryprostatin A and B as Well as Their Enantiomers and Mismatched Pairs by : Shuo Zhao
Download or read book Part I. The Enantiospecific Total Synthesis of Tryprostatin A and B as Well as Their Enantiomers and Mismatched Pairs written by Shuo Zhao and published by . This book was released on 2001 with total page 502 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Enantiospecific Total Synthesis of (+)-ajmaline and Alkaloid G as Well as Studies Directed Toward the Total Synthesis of 19-hydroxy-Nb-methylraumacline Via the Asymmetric Pictet-Spengler Reaction by : Jin Li
Download or read book Enantiospecific Total Synthesis of (+)-ajmaline and Alkaloid G as Well as Studies Directed Toward the Total Synthesis of 19-hydroxy-Nb-methylraumacline Via the Asymmetric Pictet-Spengler Reaction written by Jin Li and published by . This book was released on 1999 with total page 534 pages. Available in PDF, EPUB and Kindle. Book excerpt:
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
Book Synopsis Enantioselective Syntheses of Alkaloids from & -amino Acids by : Robert Michael Henry
Download or read book Enantioselective Syntheses of Alkaloids from & -amino Acids written by Robert Michael Henry and published by . This book was released on 1997 with total page 318 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis General Strategy for the Synthesis of Macroline/sarpagine Alkaloids by : Lin-Hua Zhang
Download or read book General Strategy for the Synthesis of Macroline/sarpagine Alkaloids written by Lin-Hua Zhang and published by . This book was released on 1990 with total page 510 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Enantioselective Total Synthesis of (+)-arborescidine C and Related Tetracyclic Indole Alkaloids Using Organocatalysis by : 賽思
Download or read book Enantioselective Total Synthesis of (+)-arborescidine C and Related Tetracyclic Indole Alkaloids Using Organocatalysis written by 賽思 and published by . This book was released on 2017 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies Toward the Enantioselective Total Synthesis of the Martinella Alkaloids by : Vivek Badarinarayana
Download or read book Studies Toward the Enantioselective Total Synthesis of the Martinella Alkaloids written by Vivek Badarinarayana and published by . This book was released on 2006 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation consists of two parts. The first part describes the enantioselective total synthesis of martinellic acid. The Martinella alkaloids have attracted considerable attention in the synthetic community over the past few years. This interest is due in large part to their unique structure and useful biological activity (bradykinin receptor antagonist). In model systems we have successfully used the [3+2] azomethine ylide-alkene cycloaddition to construct the heterocyclic core of these alkaloids. The enantioselective approach described herein also involves the azomethine ylide-alkene cycloaddition as a key step in the total synthesis. The pyrrolo[3,2-c]quinoline core of this alkaloid was constructed in an enantioselective fashion by the elaboration of an N-aryl pyrrolidinone, which was obtained via Pd-catalyzed aryl amination reaction using a non-racemic lactam. Pirkle's chiral solvating agent was successfully used to demonstrate the stereochemical integrity of not only the N-aryl lactam (obtained by Pd-catalyzed cross-coupling) but also the cycloaddition precursor and the cycloaddition product (tetracyclic pyrroloquinoline core). The tetracyclic compound obtained via the azomethine ylide-alkene cycloaddition was elaborated to ( - )-martinellic acid in 11 steps and 6% overall yield. The second part of this dissertation describes application of several novel organometallic complexes for carrying out various organic transformations. A fluorinated tris(pyrazolyl)borato silver(I) complex catalyzes the addition of ethyl diazoacetate to benzene rings, providing norcaradienes, which undergo electrocyclization to provide the corresponding cycloheptatriene (the Bu & huml;chner reaction). These reactions are surprisingly selective for addition to the aromatic moiety rather than C-H insertion. A copper complex containing a fluorinated triazapentadienyl ligand has been used to catalyze some carbene and nitrene addition and insertion chemistry. Nitrene addition occurs rapidly and with both aryl and alkyl substituted olefins providing the corresponding aziridine. The carbene transfer reactions that were attempted include C-H insertion, O-H insertion and N-H insertion, of which the latter two were very efficient.
