Progress Towards the Total Synthesis of Citrinadin A PDF Download
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Author: Elnaz Menhaji
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 472
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Book Description
Author: Elnaz Menhaji
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 472
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Book Description
Author: Martin Youngjin Pettersson
Publisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 714
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The diastereoselective formal syntheses of the corynanthe alkaloid hirsutine and oxindole alkaloid rhynchophylline are described. The general approach features the use of ring-closing metathesis (RCM) to construct an [alpha], [beta]-unsaturated lactam, which is subjected to 1,4-addition. The lithium enolate of ethyl-1,3-dithiolane-2-carboxylate was identified as the optimal nucleophile in these systems. A key feature of this approach is that the stereochemical outcome of the 1,4-addition can be effectively controlled by appropriately sequencing the indole Boc-protection step to give either the C(3)-H/C(15)-H cis or C(3)-H/C(15)-H trans stereochemical relationship. As a result, we have developed a unified approach to both the "normal" and "pseudo" corynanthe alkaloids. This finding was highlighted through the synthesis of the complete carbon skeleton of the archetypal normal corynanthe alkaloid dihydrocorynantheol. An efficient synthesis of the tricyclic spiroindolinone ABC-fragment of the marine alkaloid citrinadin A has been achieved. The synthesis relies on a novel asymmetric oxidative rearrangement of an indole to an oxindole using a chiral auxiliary on the indole nitrogen to achieve facial selectivity. The transformation proceeds via the epoxidation of the indole C(2), C(3) double bond using DMDO, followed by a silica gelmediated 1,2-epoxide rearrangement. Using this tactic, the spirooxindole of citrinadin A, which contains two adjacent quaternary centers, was formed in high yield and excellent diastereoselectivity. Efforts toward the fragment coupling of the tricyclic spiroindolinone with a 2,4,6-trisubstituted piperidine coupling partner are described.
Author: Eric Robert Ashley
Publisher:
ISBN:
Category : Electronic dissertations
Languages : en
Pages : 658
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Author:
Publisher:
ISBN:
Category : Dissertations, Academic
Languages : en
Pages : 886
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Author: Gordon Gribble
Publisher: Elsevier
ISBN: 0080914950
Category : Science
Languages : en
Pages : 497
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This is the 20th annual volume of Progress in Heterocyclic Chemistry, which covers the literature published during 2007. As with previous volumes in the series, Volume 20 will enable the reader to keep abreast of developments in heterocyclic chemistry in an effortless way.* A critical review of the heterocyclic literature published during 2007 * Presents specialized reviews * Chapters all written by leading researchers in their field
Author: Weichyun Wong
Publisher:
ISBN:
Category :
Languages : en
Pages : 554
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Author: Carilyn Torruellas-Pagan
Publisher:
ISBN:
Category :
Languages : en
Pages : 378
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Author: Jacob Edward Dander
Publisher:
ISBN:
Category :
Languages : en
Pages : 419
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This dissertation describes efforts in the field of nickel-catalyzed amide C-N bond activations and studies toward the total synthesis of dodecahedrane. Although amide C-N bonds are generally considered inert, recent progress in the activation of these bonds has allowed for their use as synthetic building blocks. Herein, several nickel-catalyzed transformations of amides and strategies to improve the practicality of these reactions are outlined. Each of these studies highlights the utility of nickel catalysis and amides in the context of organic synthesis. Furthermore, a synthetic strategy for and experimental progress toward the synthesis of dodecahedrane are reported. The realization of this total synthesis is expected to push our understanding of molecular reactivity and represent a milestone in the field of total synthesis. Chapters one, two, and three describe the development of transformations and experimental techniques that improve the scope and practicality of nickel-catalyzed activations of aryl amide C-N bonds. More specifically, chapter one describes a nickel-catalyzed alkylation of amides to access aryl-alkyl ketone products. This catalytic methodology represents a mild approach to synthesizing these products that is complementary to the Weinreb ketone synthesis. Chapter two details a strategy for the benchtop delivery of Ni(cod)2. The air- and moisture-sensitivity of this important nickel precatalyst limits its general utility. By utilizing paraffin-Ni(cod)2 capsules, a variety of nickel-catalyzed transformations, including aryl amide cross-couplings, can be performed outside of a glovebox. Chapter three outlines efforts to deploy paraffin-Ni(cod)2 capsules in an undergraduate organic chemistry laboratory. Through the use of these reagents in an esterification of an aryl amide, students gain meaningful insights into frontiers in cross-coupling research, nickel catalysis, and the use of amides in synthetic organic chemistry. Chapters four and five are concerned with the development of nickel-catalyzed transformations of aliphatic amides. Chapter four specifically details efforts to develop a nickel-catalyzed transamidation of aliphatic secondary amides. Through the use of a two-step activation-cross-coupling approach, we have achieved a mild and general solution to this long-standing problem in organic chemistry. Chapter five describes a method for performing arylations of aliphatic amides on the benchtop. By employing paraffin-Ni(cod)2/Benz-ICy[TM]HCl capsules, Suzuki-Miyaura cross-couplings of aliphatic amides to generate aryl-alkyl ketones can be achieved without the need for glovebox manipulations. Both of these studies expand the field of nickel-catalyzed amide C-N bond activations and promote amides as useful synthetic building blocks. Chapter six illustrates a chemoenzymatic approach to enantioselective transformations of amides. The development of a one-pot Suzuki-Miyaura cross-coupling and ketoreductase-mediated reduction allows for rapid, selective access to enantioenriched alcohol products from amides. This methodology represents the first enantioselective transformation of amides that relies on amide C-N bond activation and is expected to guide the development of other asymmetric transformations of amides. Finally, chapter seven details a strategy for the total synthesis of the complex hydrocarbon dodecahedrane. Our proposed symmetry-based approach to this fascinating icosahedral molecule relies on an ambitious [2+2+2+2+2] cyclization to assemble five key C-C bonds in a single synthetic operation. Current efforts to synthesize the necessary substrate for the [2+2+2+2+2] cyclization are detailed. If successful, these studies should provide efficient access to dodecahedrane and are expected to lead to insights into new modes of reactivity.
Author: Navjeet Kaur
Publisher: Elsevier
ISBN: 0443189420
Category : Science
Languages : en
Pages : 502
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Book Description
5-Membered Heterocycle Synthesis Using Iodine presents both old and new methods for the synthesis of various five-membered heterocycles using iodine, providing information for making specific compounds using particular reagents. Heterocyclic frameworks represent the main structural subunits of many biologically active compounds and natural products, and the ability of heterocycles to act both as reactive pharmacophores and biomimetics has greatly contributed to their unique value as traditional key elements of various drugs. Contemporary developments in process chemistry and discovery emphasize novel sustainable synthetic pathways as fast and ecologically acceptable alternatives to the traditional protocols. This book serves as a guide for students, pharmacologists, biochemists, organic and medicinal chemists, researchers, and academic professionals to obtain easy access to synthetic protocols for different five-membered heterocycles using iodine. - Covers the applications of five-membered heterocycles - Highlights methodologies for the synthesis of five-membered heterocycles using iodine - Contains the most up-to-date information in this fast-moving field
Author: Vijay Kumar Sharma
Publisher: Academic Press
ISBN: 0128217359
Category : Science
Languages : en
Pages : 612
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Book Description
Fungi Bio-prospects in Sustainable Agriculture: Fungal metabolites and Nano-technology is a three-volume series that has been designed to explore the huge potential of the many diverse applications of fungi to human life. The series unveils the latest developments and scientific advances in the study of the biodiversity of fungi, extremophilic fungi, and fungal secondary metabolites and enzymes, while also presenting cutting-edge molecular tools used to study fungi. Readers will learn all about the recent progress and future potential applications of fungi in agriculture, environmental remediation, industry, food safety, medicine, and nanotechnology.Volume 3 provides a comprehensive account of fungal metabolites, including bioactive and host origin compounds, along with other biomolecules, and mycotoxins. This book includes the applications, limitations, and prospects of working with fungal secondary metabolites. The authors explore fungi in the myco-mediated synthesis of nanoparticles along with their biotechnological, industrial, and agricultural uses. This book also discusses advancements in medical mycology for the diagnosis and treatment of fungal infections. Furthermore, this book provides up-to-date and in-depth knowledge about the adoption of advanced CRISPR-Cas9 technology in fungi for gene editing - Covers the secondary metabolites of fungi including bioactive compounds, mycotoxins and other biomolecules - Provides insight into the fungal mediated biosynthesis of nanoparticles and its various applications in diverse fields - Describes advances in diagnosis and treatment of human fungal infections - Presents the latest information on applications of the CRISPR-Cas9 system in fungi
