Stereoselective Synthesis of an Omuralide Analogue Through a Lewis Acid Catalyzed Reaction of an Aldehyde and an Oxazole

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Total Pages : 50 pages
Book Rating : 4.:/5 (125 download)

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Book Synopsis Stereoselective Synthesis of an Omuralide Analogue Through a Lewis Acid Catalyzed Reaction of an Aldehyde and an Oxazole by : Doris Berman

Download or read book Stereoselective Synthesis of an Omuralide Analogue Through a Lewis Acid Catalyzed Reaction of an Aldehyde and an Oxazole written by Doris Berman and published by . This book was released on 2014 with total page 50 pages. Available in PDF, EPUB and Kindle. Book excerpt: Lactacystin, or more specifically, its biologically active form, omuralide, is a known inhibitor of cell cycle progression in a number of cell lines. However, omuralide is also an inhibitor of the proteasome, an essential protease within eukaryotic cells. Because of the complexity of the available syntheses, development of selective analogs of omuralide has progressed slowly. Our research seeks to develop efficient and highly stereoselective syntheses of omuralide analogs via the metal catalyzed reaction of a chiral aldehyde with a protected oxazole.This catalysis has been accomplished with high stereoselectivity using a simple aluminum catalyst but the efficiency of this reaction has not been high. Results from a variety of additional catalysts will be discussed.

Stereoselective Synthesis: A Practical Approach

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Publisher : Wiley-VCH
ISBN 13 :
Total Pages : 410 pages
Book Rating : 4.3/5 (91 download)

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Book Synopsis Stereoselective Synthesis: A Practical Approach by : M. Nógrádi

Download or read book Stereoselective Synthesis: A Practical Approach written by M. Nógrádi and published by Wiley-VCH. This book was released on 1995 with total page 410 pages. Available in PDF, EPUB and Kindle. Book excerpt: The state-of-the-art in stereoselective synthesis! Thoroughly revised and updated, this enlarged second edition offers a plethora of valuable information on methods and reagents in stereoselective synthesis. Methods have been selected for high efficiency and selectivity; mechanistic aspects are treated succinctly, with a strong emphasis on practical applications. For this new edition, material has been added on * homogeneous diastereoselective hydrogenations * enantioselective oxidations * novel, efficient chiral auxiliaries Much of the information given is presented in figures and tables, which makes the book a valuable reference work for the practically minded organic chemist. From reviews of the first edition: 'The extensive material in the volume should prove particularly useful to anyone involved in synthetic chemistry or teaching a course in organic chemistry.' Journal of Medicinal Chemistry 'With nearly 1400 references cited, the book contains a wealth of information and should be a useful addition to the chemist's library.' The American Scientist

Classics in Stereoselective Synthesis

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Publisher : John Wiley & Sons
ISBN 13 : 9783527324521
Total Pages : 664 pages
Book Rating : 4.3/5 (245 download)

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Book Synopsis Classics in Stereoselective Synthesis by : Erick M. Carreira

Download or read book Classics in Stereoselective Synthesis written by Erick M. Carreira and published by John Wiley & Sons. This book was released on 2009-02-09 with total page 664 pages. Available in PDF, EPUB and Kindle. Book excerpt: Die wichtigsten und nützlichsten Methoden der modernen stereoselektiven Synthese sind in diesem Band zusammengefasst. Viele anschauliche Beispiele für die Darstellung von Wirkstoffen und Naturstoffen regen zur gezielten Abwandlung und Integration in eigene Synthesewege an. Dabei geht es den Autoren weniger darum, das Gebiet in seiner Gesamtheit darzustellen; vielmehr versuchen sie, die wirklich grundlegenden Ansätze auszuwählen, die jeder organische Synthesechemiker kennen und anwenden sollte.

Oxazoles, Volume 60, Part B

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Publisher : John Wiley & Sons
ISBN 13 : 0471649309
Total Pages : 716 pages
Book Rating : 4.4/5 (716 download)

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Book Synopsis Oxazoles, Volume 60, Part B by : David C. Palmer

Download or read book Oxazoles, Volume 60, Part B written by David C. Palmer and published by John Wiley & Sons. This book was released on 2004-04-15 with total page 716 pages. Available in PDF, EPUB and Kindle. Book excerpt: Synthesis, Reactions, and Spectroscopy presents a comprehensive review of the literature from 1983 to the present covering oxazoles, mesoionic oxazoles, oxazolones, oxazolines, and chiral bisoxazolines. In-depth coverage includes synthesis, reactions, spectroscopic and physical properties for each class of compounds, as well as important developments related to the use of those compounds.

Chiral Lewis Acid and Organocatalytic Methods for the Asymmetric Synthesis and Functionalization of 3,3'-oxindoles and 3,3'-spirocyclic Oxindoles

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ISBN 13 : 9781321013184
Total Pages : pages
Book Rating : 4.0/5 (131 download)

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Book Synopsis Chiral Lewis Acid and Organocatalytic Methods for the Asymmetric Synthesis and Functionalization of 3,3'-oxindoles and 3,3'-spirocyclic Oxindoles by : Joseph Jesse Badillo

Download or read book Chiral Lewis Acid and Organocatalytic Methods for the Asymmetric Synthesis and Functionalization of 3,3'-oxindoles and 3,3'-spirocyclic Oxindoles written by Joseph Jesse Badillo and published by . This book was released on 2014 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The development of regio- and stereoselective methods for the synthesis of oxindoles and spirocyclic oxindoles is important due to the prevalence of these structures in natural products and medicinal agents. This dissertation describes both Lewis acid and organocatalytic strategies for the regio-, diastereo-, and enantioselective synthesis of several classes of 3,3'-oxindoles and 3,3'-spirooxindoles. These strategies are applied to several synthetic transformations including allylsilane annulations, Friedel-Crafts alkylations, and Pictet-Spengler reactions. Chapter one describes an overview of recent methods for the enantioselective synthesis of oxindoles and spirooxindoles with a particular focus on scaffolds relevant to drug discovery. This overview is organized by type of catalyst and strategy in order to compare traditional organometallic and Lewis acid methods with recent organocatalytic methods. This chapter also features a section on multicomponent and cascade reaction strategies. Chapter two describes the development of synthetic methodology using titanium(IV)-catalysis for the selective synthesis of two new classes of spirocyclic oxindoles. In the first section, I present a highly regio- and diastereoselective method for the synthesis of spiro[3,3'oxindoleoxazolines] upon addition of 5-methoxy-2-oxazoles to isatins. In the second section, I present a method for the addition of 5-methoxy-2-aryloxazoles to [alpha],[beta]-unsaturated alkylidene oxindoles to provide access to spiro[3,3'oxindole-1-pyrrolines] with excellent yields and diastereoselectivities. This methodology is also effective for the diastereoselective synthesis of 1-pyrrolines derived from coumarins and simple malonates. Chapter three describes the condensation cyclization between isatins and 5-methoxytryptamine catalyzed by chiral phosphoric acids to provide spirooxindole tetrahydro-[beta]-carboline products in excellent yields and enantioselectivity. A comparison of catalysts provides insight for the reaction scope and factors responsible for efficient catalytic activity and selectivity in these Pictet-Spengler type spirocyclization reactions. In addition I show that chiral phosphoric acids with different 3,3'-substitution on the binaphthyl system and opposite axial chirality afford the spiroindolone product with the same absolute configuration. Chapter four describes a strategy for the efficient two-step synthesis of triazole derivatives of oxindoles and spirooxindoles. Using a common set of N-propargylated isatins, a series of mechanistically distinct stereoselective reactions with different combinations of nucleophiles and catalysts provides access to diverse hydroxy-oxindoles, spiroindolones, and spirocyclic oxazoline structures. The resulting N-propargylated oxindoles are then converted to triazoles using copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. This strategy is used for the synthesis of a 64-member pilot-scale library of diverse oxindoles and spirooxindoles. Chapter five describes the first catalytic asymmetric [3+2] allylsilane annulation for the synthesis of cyclopentanes containing an all-carbon quaternary spirocenter. The annulation reaction is catalyzed with a chiral scandium(III)-indapybox complex where a sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaBArF) anion is essential for catalytic activity and stereoselectivity. Lactone formation affords evidence for an ester stabilized [beta]-silyl carbocation. Further transformations provide access to N-H spirooxindoles and allow transformation of the silyl group to a hydroxyl moiety. This catalyst complex is also effective for the asymmetric Friedel-Crafts conjugate addition of variety of additional pi-nucleophiles (i.e. indoles, pyrroles, anilines) to [alpha],[beta]-unsaturated alkylidene oxindoles. This methodology is also effective for the diastereoselective synthesis of coumarin and simple malonate derivatives.

Stereoselective Synthesis

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ISBN 13 :
Total Pages : 756 pages
Book Rating : 4.:/5 (112 download)

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Book Synopsis Stereoselective Synthesis by :

Download or read book Stereoselective Synthesis written by and published by . This book was released on 1989 with total page 756 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Science of Synthesis: Stereoselective Synthesis Vol. 3

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Publisher : Thieme
ISBN 13 : 3131789611
Total Pages : 1172 pages
Book Rating : 4.1/5 (317 download)

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Book Synopsis Science of Synthesis: Stereoselective Synthesis Vol. 3 by : P. Andrew Evans

Download or read book Science of Synthesis: Stereoselective Synthesis Vol. 3 written by P. Andrew Evans and published by Thieme. This book was released on 2014-05-14 with total page 1172 pages. Available in PDF, EPUB and Kindle. Book excerpt: The major emphasis here is on enantioselective reactions using asymmetric catalysts. Examples from the total synthesis of various natural and unnatural targets validates the utility of the synthetic methods. Specific topics discussed: cycloaddition, cycloisomerization and sigmatropic rearrangement reactions, allylic and carbonyl functionalization reactions, metal-catalyzed cross-coupling reactions, desymmetrization, fluorination, polymerization and sulfide oxidation reactions. This volume is part of a 3-volume set: Science of Synthesis Stereoselective Synthesis Workbench Edition Further information about Stereoselective Synthesis (including sample pages and the table of contents)

Stereoselective Synthesis

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Total Pages : pages
Book Rating : 4.:/5 (96 download)

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Book Synopsis Stereoselective Synthesis by :

Download or read book Stereoselective Synthesis written by and published by . This book was released on 1988 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:

Stereoselective Synthesis Using Aminyl Radicals Derived from Alpha-amino Acids

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ISBN 13 :
Total Pages : 0 pages
Book Rating : 4.:/5 (594 download)

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Book Synopsis Stereoselective Synthesis Using Aminyl Radicals Derived from Alpha-amino Acids by : Kirk Alexander Lewis

Download or read book Stereoselective Synthesis Using Aminyl Radicals Derived from Alpha-amino Acids written by Kirk Alexander Lewis and published by . This book was released on 1997 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Oxazoles

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ISBN 13 :
Total Pages : 672 pages
Book Rating : 4.X/5 (4 download)

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Book Synopsis Oxazoles by : David C. Palmer

Download or read book Oxazoles written by David C. Palmer and published by . This book was released on 2003 with total page 672 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Studies in Natural Products Chemistry

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ISBN 13 :
Total Pages : 1094 pages
Book Rating : 4.:/5 (13 download)

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Book Synopsis Studies in Natural Products Chemistry by : Atta-ur- Rahman

Download or read book Studies in Natural Products Chemistry written by Atta-ur- Rahman and published by . This book was released on 1996 with total page 1094 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Stereoselective Synthesis

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Publisher : Studies in Natural Products Ch
ISBN 13 : 9780444893666
Total Pages : 540 pages
Book Rating : 4.8/5 (936 download)

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Book Synopsis Stereoselective Synthesis by : Atta-ur Rahman

Download or read book Stereoselective Synthesis written by Atta-ur Rahman and published by Studies in Natural Products Ch. This book was released on 1993 with total page 540 pages. Available in PDF, EPUB and Kindle. Book excerpt: Section 1

Science of Synthesis 2010: Volume 2010/9: Stereoselective Synthesis 3

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ISBN 13 : 9783131541314
Total Pages : 720 pages
Book Rating : 4.5/5 (413 download)

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Book Synopsis Science of Synthesis 2010: Volume 2010/9: Stereoselective Synthesis 3 by : P. Evans

Download or read book Science of Synthesis 2010: Volume 2010/9: Stereoselective Synthesis 3 written by P. Evans and published by . This book was released on 2011 with total page 720 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Studies in Natural Products Chemistry

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Publisher : Elsevier Science
ISBN 13 : 9780444824585
Total Pages : 1108 pages
Book Rating : 4.8/5 (245 download)

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Book Synopsis Studies in Natural Products Chemistry by : Atta-ur-Rahman

Download or read book Studies in Natural Products Chemistry written by Atta-ur-Rahman and published by Elsevier Science. This book was released on 1996-05-15 with total page 1108 pages. Available in PDF, EPUB and Kindle. Book excerpt: In Volume 18 of this well-established series, Professor Atta-ur-Rahman again brings together the work of several of the world's leading authorities in organic chemistry. Their contributions demonstrate the rapid, ongoing development of this field by illustrating many of the latest advances in synthetic methods, total synthesis, structure determination, biosynthetic pathways, and biological activity. The opening chapter presents an overview of strategies for the synthesis of several classes of natural products with an emphasis on complex polycyclic systems. Subsequent chapters discuss the synthesis of specific classes of compounds, including morphine, polyketides, acetogenins, nonactic acid derivatives, complex spirocyclic ethers, ä-lactam and pyridone derivatives, inositol phosphates, sphingolipids, brassinosteroids, Hernandia lignans, and dimeric steroidal pyrazine alkaloids. Finally, the ever stronger links between chemistry and biology are reinforced by chapters on the origin and function of secondary metabolites, bioactive conformations of gastrin hormones, and immunochemistry.

Oxazoles

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ISBN 13 :
Total Pages : 728 pages
Book Rating : 4.X/5 (4 download)

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Book Synopsis Oxazoles by : David C. Palmer

Download or read book Oxazoles written by David C. Palmer and published by . This book was released on 2004 with total page 728 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Enantioselective Organocatalysis

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Publisher : Wiley-VCH
ISBN 13 : 3527610952
Total Pages : 559 pages
Book Rating : 4.5/5 (276 download)

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Book Synopsis Enantioselective Organocatalysis by : Peter I. Dalko

Download or read book Enantioselective Organocatalysis written by Peter I. Dalko and published by Wiley-VCH. This book was released on 2007-06-27 with total page 559 pages. Available in PDF, EPUB and Kindle. Book excerpt: In this reference leaders at the forefront of research provide an insight into one of the hottest topics in organic synthesis, focusing on the most important enantioselective reactions. Clearly structured, each entry begins with a concise introduction, including a mechanistic discussion of the reaction, followed by preparative guidelines for newcomers, such as carefully selected working procedures with critical notes for bench chemists, rules of thumb and tips and tricks.

Stereoselective Synthesis of Pyrrolidinones Via Nitro-Mannich Reaction

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Total Pages : pages
Book Rating : 4.:/5 (829 download)

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Book Synopsis Stereoselective Synthesis of Pyrrolidinones Via Nitro-Mannich Reaction by : L. R. Horsfall

Download or read book Stereoselective Synthesis of Pyrrolidinones Via Nitro-Mannich Reaction written by L. R. Horsfall and published by . This book was released on 2011 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Part 1: The first section of this thesis details the stereoselective synthesis of pyrrolidinones via the nitro-Mannich reaction. Expanding on previous work within the Anderson group, conjugate addition of a diorganozinc species to nitroacrylate 141 was carried out successfully. Subsequent in situ nitro-Mannich reaction was then followed by spontaneous lactamisation to afford the desired five-membered ring pyrrolidinone structure. The reaction was performed in one pot, generating three contiguous stereocentres in a highly diastereoselective manner. The scope of the reaction was investigated by varying substituents on the imine partner. This led to the synthesis of a broad range of analogues incorporating alkyl, aryl and heteroaryl functional groups, each isolated as a single diastereoisomer in 48-84% yield. Studies to develop an asymmetric variant of the reaction were performed, with Feringa's phosphoramidite ligand 299 enabling formation of the pyrrolidinone with a moderate 52% e.e. Analysis of the reaction mechanism and the origin of the observed diastereoselectivity have been investigated, followed by further functionalisation of the pyrrolidinone structure to yield a wide range of synthetically useful building blocks. Anderson, J. C.; Stepney, G. J.; Mills, M. R.; Horsfall, L. R.; Blake, A. J.; Lewis, W. J. Org. Chem. 2011, 76, 1961 (featured article). Part 2: This section describes work towards the total synthesis of popolohuanone E (1), a marine natural product isolated from the Dysidea sp. sponge in 1990. The molecule contains a unique trihydroxylated dibenzofuran-1,4-dione core and two identical sesquiterpene units. The complex molecular structure and interesting biological activity of popolohuanone E (1) has made this compound a particularly interesting target. Synthesis of model system 132 was successfully achieved, which allowed investigations into the key oxidative dimerisation reaction. Extensive studies led to isolation of the desired bis-quinone 133 in 40% yield, followed by acid catalysed cyclisation to form the dibenzofuran core present in popolohuanone E (1), in 26% yield. Focus then turned to the synthesis of the proposed precursor to popolohuanone E (1), 6'-hydroxyarenarol (7), based on the route developed within the Anderson group. Studies began with the enantioselective synthesis of intermediate iodide 83 utilising Myers' pseudo-ephedrine auxillary. The remaining stereocentres were subsequently installed via an intramolecular Hosomi-Sakurai reaction in high yield and diastereoselectivity. With the cis-decalin framework in hand, construction of the phenolic portion was achieved by addition of lithiated 1,2,4-trimethoxybenzene to neo-pentyl aldehyde 74, followed by deoxygenation using Barton-McCombie conditions. Installation of the exo-cyclic alkene, followed by removal of the three methyl ether protecting groups, then afforded the required precursor 6'- hydroxyarenarol (7). Finally, dimerisation was attempted as developed previously on model system 132, however none of the desired bis-quinone (18) was observed.