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  • 2020-2022
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  • 1985-1989  (8)
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  • 1986  (8)
  • Synthetic methods
  • 1
    Electronic Resource
    Electronic Resource
    New Methods for the Synthesis of Glycosides and Oligosaccharides - Are There Alternatives to the Koenigs-Knorr Method? [New Synthetic Methods (56)]Dedicated to Professor Rudolf Gompper on the occasion of his 60th birthday (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 212-235 
    Details
    ISSN: 0570-0833
    Keywords: Glycosides ; Oligosaccharides ; Koenigs-Knorr method ; Synthetic methods ; Carbohydrates ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Glycoproteins, glycolipids, and glycophospholipids (glycoconjugates) are components of membranes. The oligosaccharide residue is responsible for intercellular recognition and interaction; it acts as a receptor for proteins, hormones, and viruses and governs immune reactions. These significant activities have stimulated interest in oligosaccharides and glycoconjugates. With their help it should be possible to clarify the molecular basis of these phenomena and to derive new principles of physiological activity. Major advances in the synthesis of oligosaccharides have been made by the use of the Koenigs-Knorr method, in which glycosyl halides in the presence of heavy-metal salts are employed to transfer the glycosyl group to nucleophiles. The disadvantages of this procedure have led to an intensive search for new methods. Such methods will be discussed in this article. Emphasis is placed on glycoside and saccharide formation by 1-O-alkylation, on the trichloroacetimidate method, and on activation through the formation of glycosylsulfonium salts and glycosyl fluorides.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198602121
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  • 2
    Electronic Resource
    Electronic Resource
    Organic Synthesis at High Temperatures. Gas-Phase Flow Thermolysis [New Synthetic Methods (57)]Part of the Habilitationsschrift, M. Karpf, Universität Zürich 1984. (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 414-430 
    Details
    ISSN: 0570-0833
    Keywords: Gas-phase flow thermolysis ; Thermolysis ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The preference for carrying out synthetic organic reactions at the lowest possible temperature is due to the expectation that the selectivity often increases with decreasing temperature, as is confirmed by many examples and also theoretically justified. Selectivity, however, is not the only problem at high temperatures; further factors include the frequently limited thermal stability of the functional groups and structural elements not directly involved in the transformation. In spite of these limitations, the advantages of high temperatures and the greatly improved knowledge of the mechanisms of dynamic gas-phase processes accumulated in recent years can be exploited in directed organic synthesis. In this review the synthetic potential of gas-phase flow thermolysis will be described from the viewpoint of the synthetic chemist with the aid of typical examples of application.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198604141
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  • 3
    Electronic Resource
    Electronic Resource
    The Palladium-Catalyzed Cross-Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)] (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 508-524 
    Details
    ISSN: 0570-0833
    Keywords: Cross-coupling ; Organotin compounds ; Electrophilicity ; Palladium ; Catalysis ; C-C coupling ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The cross-coupling of organotin reagents with a variety of organic electrophiles, catalyzed by palladium, provides a novel method for generating a carbon-carbon bond. Because this mild, versatile reaction is tolerant of a wide variety of functional groups on either coupling partner, is stereospecific and regioselective, and gives high yields of product, it is ideal for use in the synthesis of elaborate organic molecules. When the coupling reaction is carried out in the presence of carbon monoxide, instead of a direct coupling, carbon monoxide insertion takes place, stitching the two coupling partners together and generating a ketone.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198605081
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  • 4
    Electronic Resource
    Electronic Resource
    Hydroxide Ion Initiated Reactions Under Phase Transfer Catalysis Conditions: Mechanism and Implications. New Synthetic Methods (62) (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 960-970 
    Details
    ISSN: 0570-0833
    Keywords: Phase-transfer catalysis ; Catalysis ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The development of Phase Transfer Catalysis (PTC) represents a major step forward in the employment of many organic reactions and renders them very convenient and useful processes. These reactions involve the application of nucleophiles in general, anions and bases in particular, in reactions carried out in a water-organic solvent system. They can be performed both in the laboratory and on an industrial scale. The ease of application of PTC processes is the main reason for their increasing utilization in industry. An outstanding achievement of this technique is the employment of aqueous bases in reactions which traditionally would otherwise require a strong base in a nonaqueous medium. The classical procedures that require severe anhydrous conditions, expensive solvents and dangerous bases such as metal hydrides and organometallic reagents are now replaced by aqueous solutions of, e.g., sodium or potassium hydroxides (PTC/OH processes). In contrast to the extensive synthetic applications of PTC/OH systems, the detailed mechanisms of these processes have been the subject of a great deal of controversy and various mechanisms have been suggested. However, it would seem that our knowledge concerning the mechanistic aspects of such reactions has now reached the stage where it can be used to advantage in synthesis planning. A better understanding of the various factors which influence the reaction would undoubtedly help to optimize PTC/OH processes such as to enable higher yields in shorter reaction times at lower temperatures. The importance of, inter alia, the catalyst will be pointed out and it is highly recommended that such catalysts be always available in the laboratory, for the range of organic reactions that they can efficiently, conveniently and safely catalyze is vast indeed.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198609601
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  • 5
    Electronic Resource
    Electronic Resource
    [3+2] Cycloaddition Approaches to Five-Membered Rings via Trimethylenemethane and Its Equivalents [New Synthetic Methods (55)] (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 1-20 
    Details
    ISSN: 0570-0833
    Keywords: Cycloaddition ; Trimethylenemethane ; Synthetic methods ; Cyclopentanes ; Heterocycles ; Natural products ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The power of cycloadditions for ring formation derives from the potential for chemo-, regio-, diastereo-, and enantioselectivity. Trimethylenemethane (TMM) and its equivalents offer the possibility of extending such benefits to the synthesis of five-membered rings. Three types of conjunctive reagents appear to be promising candidates: (1) selected 4-alky-lidene-4,5-dihydro-3H-pyrazoles, (2) 2-[(trimethylsilyl)methyl]allyl esters and halides, and (3) alkylidenecyclopropanes. Thermal reactions, especially intramolecular ones, effect the cycloaddition of the pyrazoles to olefins-especially electron-poor olefins. The latter two precursors require a catalyst, notably a palladium complex, to unlock the synthetic potential. With the 2-[(trimethylsilyl)methyl]allyl esters, a general chemo-, regio-, and diastereoselective cycloaddition with typical Diels-Alder dienophiles forms methylenecyclopentanes in both inter- and intramolecular fashion. A tin analogue allows extension of this cycloaddition to aldehydes, and, in a related sequence, to ketones and imines to form 3-methylenete-trahydrofurans and 3-methylenepyrrolidines with excellent diastereoselectivity. The 2-[(tri-methylsilyl)methyl]allyl esters also serve to effect net methylenecyclopentane annulation to cyclic enols. Such adducts can further undergo three-carbon intercalation or combined ring contraction-spiroannulation simply by the use of either a nucleophilic or electrophilic trigger. Alkylidenecyclopropanes undergo cycloadditions to both electron-rich and electron-poor olefins when stimulated by metal catalysts, especially palladium. A complementary regiochemistry to the approach based upon silicon conjunctive reagents is observed. The availability of these cycloadditions provides new strategies for the synthesis of natural products.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198600013
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  • 6
    Electronic Resource
    Electronic Resource
    Indirect Electroorganic Syntheses - A Modern Chapter of Organic Electrochemistry [New Synthetic Methods (59)] (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 683-701 
    Details
    ISSN: 0570-0833
    Keywords: Electroorganic synthesis ; Electrochemistry ; Synthetic methods ; Redox chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The electrochemical formation and regeneration of redox agents for organic syntheses (indirect electrolysis) widens the potential of electrochemistry, as higher or totally different selectivities can often be obtained while at the same time the energy input can be lowered significantly. Higher current densities can also be obtained by preventing otherwise often encountered electrode inhibition. New types of redox catalysts can be formed in-situ and can be regenerated after reaction with the substrates. This principle is of increasing importance also for the application of already known redox agents with regard to environmental protection, since large amounts of a product can be generated in a closed circuit using only relatively small amounts of the redox reagent. Consequently the operation of such a process can be greatly simplified, and the release of ecologically objectionable spent reagents into the environment can be prevented. The broad spectrum of redox catalysts currently in use includes, inter alia, metal salts in very low or high oxidation states, halogens in various oxidation states, and, in particular, a wide variety of transition-metal complexes. A great deal of progress has recently been made in the application of organic electron transfer agents, since compounds have been found that are sufficiently stable in both the reduced as well as the oxidized state.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198606831
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  • 7
    Electronic Resource
    Electronic Resource
    Total Synthesis of Anthracyclinone [New Synthetic Methods (60)]Dedicated to Professor Albert Mondon on the occasion of his 70th birthday (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 790-807 
    Details
    ISSN: 0570-0833
    Keywords: Anthracyclinones ; Synthetic methods ; Antibiotics ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The remarkable antitumor properties of anthracycline antibiotics have motivated synthetic chemists, and a large number of groups have been active recently in this field. Initially, there was very little hope for this class of substances due to their extreme toxicity. However, the dividing line between toxicity and desired pharmacological effect has broadened to such an extent, partly through microbiological methods (new strains, mutants) and partly through semisynthetic modifications, that today anthracyclines take number one place (over 20% of the market) in the chemotherapy of (human) cancer. The demands made on modern cytostatica are extremely high, as may be seen from the fact that of the more than 600000 drugs tested in animals, only about 40 are in clinical use. In the meantime, some anthracyclines obtained by total synthesis are also in clinical testing. In this review it will hopefully be demonstrated that all those concerned in the chemotherapeutic use of these substances have also contributed to the general progress made in the solution of regio- and stereo-chemical problems of linearly annelated ring systems.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198607901
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  • 8
    Electronic Resource
    Electronic Resource
    Selective Synthesis by Use of Lewis Acids in the Presence of Organocopper and Related Reagents. New Synthetic Methods (61) (1986)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 25 (1986), S. 947-959 
    Details
    ISSN: 0570-0833
    Keywords: Lewis acids ; Synthetic methods ; Selectivity ; Organocopper compounds ; Addition ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Organometallic compounds with pronounced nucleophilicity such as organocopper and organolithium compounds, and powerful electrophiles, such as BF3 and AlCl3, are generally thought to be incompatible under normal, homogeneous reaction conditions. As a matter of course, it is anticipated that the two species cannot coexist and undergo transmetalation reactions. To our surprise, however, RCu and BF3 are compatible at low temperature. RCu·BF3 and related organocopper-Lewis acid reagents exhibit new and unique reactivities and selectivities: in conjugate additions, e.g., not only activation but also high regio-, stereo-, and chemo-selectivity as well as very high asymmetric induction is observed; allylic derivatives are alkylated regioselectively, and reaction towards carbonyl groups, imines, epoxides, aziridines, ethers, acetals, orthoformates, and pyridinium salts is in each case found to be selective. RLi·BF3 and related organolithium-Lewis acid reagents also exhibit noteworthy selectivities and reactivities. These complex reagents are utilized in the key steps of the total synthesis of many important natural products, such as certain terpenes, steroids, and alkaloids.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198609473
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