Stereoselective synthesis

著者

• Rahman, Atta-ur-

書誌事項

Stereoselective synthesis

edited by Atta-ur-Rahman

（Studies in natural products chemistry / edited by Atta-ur-Rahman, v. 1, 3, 4, 6, 8, 10, 11, 12, 14, 16, 18）

Elsevier, 1988-

• pt. A
• pt. B
• pt. C
• pt. D
• pt. E
• pt. F
• pt. G
• pt. H
• pt. I
• pt. J
• pt. K

注記

Includes bibliographies and index

内容説明・目次

巻冊次

pt. A ISBN 9780444429704

内容説明

This first volume deals with stereoselective synthesis of a wide variety of complex natural products. It contains 17 high quality contributions by leading exponents in the field providing organic chemists with interesting and informative accounts of the current state of the art.

目次

Indolocarbazole alkaloids (J. Bergman). Pentacyclic Strychnos indole alkaloids (J. Bosch, J. Bonjoch). Synthetic studies in the field of indole alkaloids (M. Lounasmaa). Synthesis of zwitterionic indolo[2,3-a]quinolizine alkaloids (G.W. Gribble). Vinyl azides in natural products synthesis (C.J. Moody). Synthesis of some isoquinoline alkaloids via 8,14-cycloberbines (M. Hanaoka). The synthesis of 1-azabicylic alkaloids (Y. Nishimura). Synthesis of potent antitumor alkaloids isolated from Sesbania drummondi seeds (F. Matsuda, S. Terashima). The synthesis of pyrrolidine-containing natural products via [3+2] cycloadditions (W.H. Pearson). Total synthesis of nitrogen-containing natural products via cycloaddition reactions (C. Kibayashi). Synthetic approaches to complex nucleoside antibiotics (Ph.P. Garner). Studies directed toward the total synthesis of the milbemycins and avermerctins (M.T. Crimmins et al.). Stereoselective synthesis of biologically active compounds (A.V. Rama Rao). Tropone: versatile building block for natural product synthesis (J.H. Rigby). Homochiral ketals and acetals in organic synthesis (E.A. Mash). Recent advances in biomimetic olefin cyclization using mercury (II) triflate/amine complex (M. Nishizawa). Chiral synthesis of bioactive natural products employing the building blocks of microbial origin (K. Mori). Subject Index.

巻冊次

pt. I ISBN 9780444817808

内容説明

This volume contains discourses on the stereoselective synthesis of the anticancer anthracycline antibiotics, tetramic acid antibiotics, 3-4-deoxyhexoses, polysaccharides, levoglycosenone as precursor to natural products, synthesis of oligoribonucleotides, oxidation of guaiazulene, synthesis of hydroazulene sesquiterpenes and thujone as the starting point for the synthesis of natural products. The synthesis of eudesmenols, asymmetric synthesis using chiral acetals and chiral sulfoxide auxiliary and the asymmetric construction of versatile chiral precursors is presented. Chapters on cyclopentannelation reactions, chiral construction of quaternary carbons, organic synthesis involving hydrogen abstraction reactions, synthesis of taxodione, indole alkaloids, lupine and nitraria alkaloids, and benzo[c]phenanthridine alkaloids should also prove of interest to readers. The last chapter describes the major synthetic achievements during the last three decades in the synthesis of the binary anti-tumor alkaloids, vinblastine and vincristine.

目次

• Stereoselective syntheses of doxorubicin and related compounds, D.M.S. Wheeler and M.M. Wheeler
• total synthesis of nogalamycin congeners and their related compounds, F. Matsuda and S. Terashima
• synthesis of the tetramic acid antibiotics, S.J. Shimshock and P. DeShong
• the synthesis of 3-and 4-deoxy-hexoses, D. Fattori and P. Vogel
• recent developments in the synthesis of polysaccharides and stereospecificity of glycosylation reactions, N.K. Kochetkov
• levoglucosenone - a versatile carbohydrate precursor for the synthesis of natural products, Z.J. Witczak
• chemical synthesis of branched oligoribonucleotides and their related compounds, M. Sekine
• oxidation products of guaiazulene and other azulenic hydrocarbons, Y. Matsubara et al
• synthesis of hydroazulene sesquiterpenes via rearrangement of substituted hydronaphthalene precursors, L.H.D. Jenniskens et al
• a chapter in thujone chemistry - from waste by-product to natural products and related compounds, J.P. Kutney
• the total synthesis of eudesm-11 -en-4-ols, R.P.W. Kesselmans et al
• asymmetric synthesis using chiral acetals from C[2]-symmetric diols and its application to natural product synthesis, H. Fujioka and Y. Kita
• asymmetric synthesis of some natural spiro compounds utilizing chiral sulfoxide auxiliary, T. Imanishi and C. Iwata
• asymmetric construction of versatile chiral building blocks and their application to the synthesis of natural products, Y. Hirai and T. Momose
• cationic cyclopentannelation reactions, M.A. Tius
• chiral construction of quaternary carbons through addition-elimination process - application to the natural product syntheses, K. Fuji
• organic synthesis using hydrogen atom abstraction reactions, G.A. Kraus and M.D. Schwinden
• taxodione synthetic studies, A.K. Banerjee and M.C. Carrasco
• synthetic studies in the field of indole alkaloids - part 2, M. Lounasmaa
• stereoselectivity in synthesis and biosynthesis of Lupine and Nitraria alkaloids, M.J. Wanner and G.J. Koomen
• biomimetic synthesis of benzo[c]phenanthridine alkaloids from protoberberines, M. Hanaoka and C. Mukai
• synthetic approaches to vinblastine and vincristine - anticancer alkaloids of catharanthus roseus, A.U. Rahman et al.

巻冊次

pt. J ISBN 9780444822642

内容説明

Hardbound. Natural product chemistry continues to be a treasure-house of a growing diversity of natural products, many with interesting biological activities. The present volume, the 16th in the series, contains comprehensive reviews on synthetic approaches to the antitumor antibiotics actinobolin and bactobolin, fredericamycin A, the glycosidase inhibitor siastatin A, enantioselective synthesis of irodoids and brassinosteroids, use of organopalladium compounds in the synthesis of prostaglandins and alkaloids as well as the synthesis of amino acids using transition metal organometallic methods.The book also covers recent advances in the synthesis of piperidine and indolizidine alkaloids, aporphine alkaloids, neolignans, pterocarpans, 2-aryl-2,3-dihydrobenzoquinones, photooxygenation of 4-substituted phenols, and the use of furan, -butyrolactones and fluoro- -lactams in natural product synthesis.

巻冊次

pt. K ISBN 9780444824585

内容説明

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, a-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.

目次

Strategies for the Stereocontrolled De Novo Synthesis of Natural Prdoucts (L.A. Paquette). A Historical Perspective of Morphine Synthesis (T. Hudlicky et al. ). New Developments in the Synthesis of Polyketides and of Chiral Methyl Groups (J. Mulzer). Total Stereoselective Synthesis of Acetogenins of Annonaceae: A New Class of Bioactive Polyketides (B. Figadere, A. Cave). The Synthesis of Nonactic Acid. Its Derviatives and Nonactin itself (I. Fleming, S.K. Ghosh). Total Synthesis of Bioactive Natural Spiroethers, Tautomycin and Oscillatoxin D (A. Ichihara et al. ). Aza-Annulation of Enamine Related Substrates with alpha,beta-Unsaturated Carboxylate Derivatives as a Route to the Selective Synthesis of delta-Lactams and Pyridones (J.R. Stille, N.S. Barta). Selective Reactions and Total Synthesis of Inositol Phosphates (Y. Watanabe). Synthesis of Phytosphingolipids (T. Kamikawa). New Developments in Brassinosteroid Research (G. Adam et al. ). Structure Elucidation and Synthesis of the Lignans from the Seeds of Hernandia ovigera L. (M. Arimoto et al. ). Studies on the Absolute Configuration of Some Liverwort Sesquiterpenoids (M. Tori). Bioactive Gymnemic Acids and Congeners from Gymnema sylvestre (S.B. Mahato). Theory of the Origin, Function, and Evolution Secondary Metabolites (C. Christophersen). The Celastraceae from Latin America Chemistry and Biological Activity (O. Munoz et al. ). Structural Chemistry of Glycolipids from Fungi and Protozoa (E.B. Bergter, M.H.S.V. Boas). Potential Bioactive Conformations of Hormones of the Gastrin Family (L. Moroder, J. Lutz). When Two Steroids are Better than One: The Dimeric Steroid-Pyrazine Marine Alkaloids (A. Ganesan). Human IgG1 Hinge-Fragment as a Core Structure for Immunogens (L. Moroder et al. ). 13 C-NMR Spectroscopy of Coumarins and their Derivatives: A Comprehensive Review (B. Mikhova, H. Duddeck).

巻冊次

pt. B ISBN 9780444872982

内容説明

This is the second volume to be devoted to the area of stereoselective synthesis. It reviews and highlights important and new contributions by eminent scientists on a wide variety of organic reactions and strategies to the stereoselective synthesis of complex structures which will provide stimulating reading for many synthetic organic chemists.

目次

Synthesis of natural products containing five-membered rings. An evolution of general methodology (T. Hudlicky et al.). Synthetic studies on natural products possessing eight- or nine-membered rings (T. Oishi, Y. Ohtsuka). Total synthesis of polyquinane terpenes (S. Ito et al.). New synthetic methodology. The trityl salts catalyzed stereoselective Michael reaction leading to natural products (T. Mukaiyama, S. Kobayashi). New methodology for the synthesis of biologically active lactones (C.W. Jefford et al.). The aureolic acid antitumor antibiotics: a challenge for organic synthesis (R.W. Franck, S.M. Weinreb). Recent developments in modern synthetic carbohydrate chemistry (Z.J. Witczak). Recent applications of sigmatropic reactions to the synthesis of highly-oxygenated natural products (J. Kallmerten, M.D. Wittman). A formal total synthesis of colchicine (E. Wemkert, H.-S. Kim). Natural and synthetic antitumor agents: synthetic studies on CC-1065 and functionally related agents (R.S. Coleman, D.L. Boger). Recent advances on the synthesis of quinolone skeleton by [4+2] cycloaddition reaction and its application to the natural products synthesis (T. Kametani, H. Kasai). Synthesis of yohimbine and related alkaloids (I. Ninomiya, O. Miyata). Synthesis of natural products via arynes (L. Castedo, E. Guitian). Synthesis of Erythrina alkaloids (Y. Tsuda, T. Sano). The structures, reactions and syntheses of arteannuin (Qinghaosu) and related compounds (W.-S. Zhou, X.-X. Xu). Subject Index.

巻冊次

pt. C ISBN 9780444880338

内容説明

The exciting advances achieved in the area of stereoselective synthesis in recent years are illustrated by the applications to natural product chemistry presented in this book. The third volume to be devoted to this topic, it contains contributions by many eminent chemists and describes the stereoselective and enantioselective approaches to a variety of complex and challenging natural products.

目次

A general strategy for the synthesis of alkaloids of the Aizoaceae and Amaryllidaceae families (S.F. Martin). Recent developments in the synthesis of vindoline and vindoline-like compounds (B. Danieli, G. Lesma, G. Palmisano). Total synthesis of cytotoxic cyclic peptides of marine origin (T. Shioiri, Y. Hamada). From a-amino acids to amino sugars (J. Jurczak, A. Golebiowski). Higher carbon sugars (J.S. Brimacombe). The synthesis of the heptose region of gram-negative bacterial core oligosaccharides (K. Dziewiszek, A. Banaszek, A. Zamojski). Hexopyranose nucleosides (K. Antonakis). Synthesis of oligonucleotides (T. Tanaka, M. Ikehara). Total synthesis of enantiomerically pure anthracyclinones (K. Krohn, V.S. Ekkundi). The synthesis of prenylated phenolic compounds (M.A. Vela, N.H. Fischer). Highly efficient syntheses of natural drimanic sesquiterpenes, (+)-confertifolin, (+)-isodrimenin, (+)-euryfuran, and (-)-warburganal (T. Nakano). Synthesis of thienamycin and related beta-lactams from 3-hydroxybutyric acid (G.I. Georg). Optically active sulfoxides and low-valent titanium in asymmetric synthesis of natural products (G. Solladie). Benzyne cyclisation revisited (S.V. Kessar). Natural product synthesis via phosphonium ylides (H.J. Bestmann). Synthesis of bioactive natural products through the Diels-Alder reaction (A. Ichihara). Remote functionalization of camphor: synthesis of chiral intermediates for natural product synthesis (T. Money). New chemistry of vitamin C (G. Fodor, K. Sussangkarn). Subject Index.

巻冊次

pt. D ISBN 9780444885661

内容説明

The synthesis of complex natural products has attracted the efforts of the foremost organic chemists, both because many natural products have exhibited significant biological activity and because they have taxed the ingenuity of many brilliant minds towards developing synthetic routes to them. During the last decade, organic synthesis has evolved in an accelerated manner, particularly in the field of stereoselective methods for the synthesis of natural products of increasing complexity. The present volume is the fourth devoted to stereoselective synthesis. The articles included in the book cover the synthetic approaches to marine terpenoids, allenic and acetylenic carotenoids, gibberellins, antheridiogens, fungal metabolites, macrocycle antibiotics, sugar analogues, peptidoglycan analogues, chemical defense agents in ants, medium sized ring heterocycles, Strychnos alkaloids, semiochemicals and bioregulators. The authoritative reviews are all written by distinguished scientists and will undoubtedly prove to be informative and interesting.

目次

Foreword. Total synthesis of polycarbocyclic marine terpenoids (J.D. Martin). Stereoselective total syntheses of spongian-type diterpenes and scalarane-type sesterterpenes of metabolites from marine sponge organisms (T. Nakano). Allenic and acetylenic carotenoids (S. Liaaen-Jensen). Synthetic studies on gibberellins and antheridiogens (L.N. Mander). Recent advances in the chemistry of secondary metabolites isolated from Fusarium species (M.E. Savard et al.) Amphotericin B: synthetic studies (O.S. Chizhov). Development of dithioacetal S-oxides and S,S-dioxides as synthetic reagents (K. Ogura). Sugar analogs containing carbon-phosphorus bonds (H. Yamamoto, T. Hanaya). Syntheses and reactions of sugar-peptide structures related to cell-wall peptidoglycan from bacteria (D. Keglevic). Chemical defense in ants (J.C. Braekman, D. Daloze). Some aspects of heterocyclic chemistry related to isoquinoline-derived alkaloids (J.B. Bremner). Alkaloids of Strychnos dinklagei: structure and chemistry (S. Michel et al.). Chiral synthesis of natural products as semiochemicals and bioregulators (T. Kitahara). Subject Index.

巻冊次

pt. E ISBN 9780444889676

内容説明

The vast diversity of structures encountered among natural products is a constant challenge to the ingenuity of the organic chemist. The present volume is the eighth in the series, and the fifth devoted to stereoselective synthesis. The contributions in the book cover synthetic approaches to target molecules having adjacent quaternary carbon centers, applications of titanium-induced coupling reactions in the synthesis of diterpenes, synthesis of phosphopolyprenols, the use of anodic oxidation of phenols in the synthesis of natural products, synthesis of terpenes, bisabolones and gibberellins, applications of asymmetric Diels-Alder reactions, synthetic approaches to macrocycles, chemistry of tricarbonyl compounds and cycloisomerisations as well as sequential Michael additions in natural product synthesis. Synthetic approaches to indole alkaloids, thio-oligosaccharides, norepinephrine derivatives, carcinogenic adducts of DNA and thymosins are presented. The stereochemistry and mechanism of methylmuconate pathways are also described. The articles are written by eminent scientists and will be of interest to all researchers dealing with natural products.

目次

Original synthesis of molecules containing adjacent quaternary carbons (A. Krief et al.). Cembrane diterpene synthesis using titanium-induced carbonyl coupling reactions (J.E. McMurry, R.G. Dushin). Terpene synthesis (E. Wenkert). Synthesis, relative and absolute configuration of some natural bisabolones (W. Kreiser). Phosphopolyprenols and their glycosyl esters: chemical synthesis and biochemical application (L.L. Danilov, V.N. Shibaev). New aspects in synthesis of gibberellins (G. Adam et al.). Cyclopentanoid natural products via asymmetric Diels-Alder reactions (G. Helmchen et al.). Total synthesis of natural products by using anodic oxidation of phenols as a key step (Y. Shizuri et al.). Natural products syntheses by using macrocyclically controlled reactions (T. Takahashi). Heteroatom mediated synthesis of large ring compounds (E. Vedejs). Occurrence and synthesis of macrocyclic semiochemicals (E. Czyzewska, A.C. Oehlschlager). Application of the chemistry of vicinal tricarbonyl compounds in the synthesis of products of biological interest (H.H. Wasserman, C.B. Vu). Cycloisomerization of enynes as a valuable tool for the synthesis of natural products (B.M. Trost). Synthetic studies in the alkaloid field (F. Soti et al.). The methylmuconate pathways, stereochemistry and mechanism of enzymic reactions (G.W. Kirby, R.B. Cain). Thio-oligosaccharides: their synthesis and reactions with enzymes (J. Defaye, J. Gelas). A metal-free thermal glycosylation and synthetic study of cyclo-L-rhamnohexaose, the first L-cyclooligosaccharide (N. Nishizawa). Synthesis and chemistry of carcinogenic adducts of DNA (F. Johnson). Novel conformationally restricted analogs of norepinephrine: synthesis and structure activity (F.Z. Basha). Sequential Michael additions in the synthesis of natural products (D. Spitzner). Strategies for the total syntheses of thymosins (W. Voelter, A. Kapurniotu). Asymmetric synthesis via chiral organoboranes - an unexpected bonus from a half-century of borane research (H.C. Brown). Subject Index.

巻冊次

pt. H ISBN 9780444893666

内容説明

Studies in Natural Products Chemistry Volume 12: Stereoselective Synthesis (Part H) reviews the stereoselective synthetic and mechanistic chemistry of bicyclomycin. It discusses chemical studies of the taxane diterpenes; the synthetic methodology for 2-amino alcohols of biological interest; and the synthesis and structure of hydroxylated indolizidines. Some of the topics covered in the book are the synthetic routes to the oxahydrindene subunit of the avermectin-milbemycin family of antiparasitic agents; isolation, structure elucidation, biosynthesis, and biological activity of the avermectins; two-stage coupling process of macrolide antibiotics synthesis; and synthesis of the rifamycin S ansa-chain compound. The complete synthesis of erythromycin A is also covered. The role of isocyanides in the synthesis of beta lactam antibiotics and the characteristics of the beta lactam antibiotics are discussed. The development of an A-Ring annulation strategy for taxane synthesis is also presented. A chapter is devoted to the advances in the synthesis of tumor-promoting diterpenes. The book can provide useful information to chemists, biologists, students, and researchers.

目次

Preface Foreword Contributors Synthetic Routes to the Oxahydrindene Subunit of the Avermectinmilbemycin Family of Antiparasitic Agents: A Review A New Tandem Process and its Application to the Syntheses of Macrolide Antibiotics Stereoselective Synthetic and Mechanistic Chemistry of Bicyclomycin The Role of Isocyanides in the Synthesis of ss-Lactam Antibiotics and Related Compounds Synthesis of the 1ss-Methylcarbapenem Key Intermediates Chemical Studies of the Taxane Diterpenes Recent Advances in the Synthesis of Tumor-Promoting Diterpenes Hydroxylated Indolizidines and Their Synthesis A Survey of Indolo [2,3-a] Carbazole Alkaloids and Related Natural Products Synthetic Methodology For 2-Amino Alcohols of Biological Interest Stereoselective Synthesis of Natural Products Via Cationic and Radical Intermediates Subject Index

巻冊次

pt. F ISBN 9780444895585

内容説明

Studies in Natural Products Chemistry, Volume 10: Stereoselective Synthesis (Part F) is a collection of articles about studies on important organic molecules. The book covers studies such as that on the synthesis of cembranes as well as its natural occurrence and bioactivity; the stereoselective synthesis of Vitamin D; the synthesis of isoquinolinequinone antibiotics; and the nucleophilic addition chemistry of polyunsaturated carbonyl compounds. Also covered in the book are subjects such as developments in the synthesis of medium ring ethers; the biological properties, chemistry, and synthesis of didemnins; and natural products synthesis based on novel ring transformation. The text is recommended for organic chemists who would like to know more about the progresses in the study of important organic molecules and their implications in different fields.

目次

Studies on the Synthesis of Cembranes Stereoselective Synthesis of Vitamin D Synthesis of Isoquinolinequinone Antibiotics Extended Conjugate Addition Reactions: The Synthesis and Nucleophilic Addition Chemistry of Polyunsaturated Carbonyl Compounds Recent Developments in the Synthesis of Medium Ring Ethers The Didemnins: Biological Properties, Chemistry and Total Synthesis Natural Products Synthesis Based on Novel Ring Transformation Recent Developments in C-Glycoside Synthesis Natural Product Synthesis Starting with Carbohydrates Based on the Claisen Rearrangement Protocol The Synthesis of Blood Group I and I Active Oligosaccharides Glycosidase and Glycosyltransferase Inhibitors Synthesis of Oxetanocin, Novel Nucleoside Containing An Oxetane Ring, And Its Carbocyclic Analogues Biomimetic Synthesis of Macrocyclic Oligopeptides Having Isodityrosine and Related Units Asymmetric Synthesis of Chiral Alkaloids Using Chiral Sulfur Reagents

巻冊次

pt. G ISBN 9780444897442

内容説明

The current volume presents a variety of synthetic strategies developed for important classes of natural products such as taxanes, quassinoids, polyketides, macrolides, indolizidine and Aristotelia alkaloids, fungal metabolites, vitamin D analogues and higher sugars.

目次

Studies directed toward the total synthesis of the taxanes (L.A. Paquette). Synthetic approaches toward antitumor quassinoids (T. Murae, M. Sasaki). Biomimetic syntheses of aromatic natural products via polyketides (M. Yamaguchi). Conformational control in macrolide synthesis (N. Nakajima, O. Yonemitsu). Stereochemical aspects of natural product biosynthesis (K.A. Reynolds, H.G. Floss). Some chiral approaches to syntheses of bioactive indolizidine alkaloids (C. Kibayashi). Aristotelia alkaloids: synthetic and biomimetic studies (H.-J. Borschberg). Total synthesis of (+) -mevinolin and (+) -compactin (D.L.J. Clive et al.). Synthetic studies on active forms of vitamin D and their analogs (Y. Tachibana, M. Tsuji). Synthesis of natural products via alpha-halo boronic esters (D.S. Matteson). Aspects of modern higher carbon sugar synthesis (G. Casiraghi, G. Rassu). Subject Index.

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詳細情報

• NII書誌ID(NCID): BA04899495
• ISBN:
  • 0444429700
  • 0444872981
  • 044488033X
  • 0444885668
  • 0444889671
  • 0444895582
  • 0444897445
  • 0444893660
  • 0444817808
  • 044482264X
  • 0444824588
• LCCN: 88011188
• 出版国コード: ne
• タイトル言語コード: eng
• 本文言語コード: eng
• 出版地: Amsterdam ; Tokyo
• ページ数/冊数: v.
• 大きさ: 25 cm
• 分類:
  • LCC : QD415.A2
  • DC19 : 547.7
• 件名:
  • LCSH : Natural products
  • MESH : Stereoisomers
• 親書誌ID:
  • BA04899553