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  • 1
    Electronic Resource
    Electronic Resource
    The Enchanting Alkaloids of YuzurihaThis review article grew out of a series of lectures presented in Germany in July 1990, as the Merck-Schuchardt Lectureship. The full details of our work on the total synthesis of Daphniphyllum alkaloids are reported in a series of articles recently published in the Journal of Organic Chemistry: see ref. [1]. (1992)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 31 (1992), S. 665-681 
    Details
    ISSN: 0570-0833
    Keywords: Alkaloids ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The oriental plant Yuzuriha (Daphniphyllum macropodum) elaborates a fascinating family of polycyclic, squalene-derived alkaloids that provide a test for state-of-the-art methods of organic synthesis. The intriguing structures of these natural products have inspired us to design and explore two rather different approaches for their laboratory synthesis. This article recounts and contrasts these two different syntheses. The first approach was based on a method of synthetic design that emphasizes efficient construction of the polycyclic skeleton of the molecule (Corey's “network analysis”). A strategic bond was identified and the synthesis planned around the late formation of this bond. The synthesis that was designed by this approach proceeded smoothly until the point where it was necessary to remove functional groups that had been incorporated solely for the purpose of forming the strategic bond. Although the problems were eventually overcome, the resulting synthesis was too long and did not control the configuration of one of the stereocenters. The second approach was based on a possible biosynthesis of one of the alkaloids and provided surprisingly easy access to the simpler members of the family. The success of this synthesis led to a concrete proposal about the biosynthesis of the alkaloids and to the discovery of the astonishing transformation depicted in Scheme 27. In this marvelous reaction, an acyclic squalene derivative is converted by successive treatment with ordinary commodity chemicals into a pentacyclic alkaloid. The transformation involves the formation of four carbon-carbon bonds, two carbon-nitrogen bonds, and one carbon-hydrogen bond!
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.199206653
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Ring Closures with Carbon Monoxide (1966)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 5 (1966), S. 435-446 
    Details
    ISSN: 0570-0833
    Keywords: C-C coupling ; Ring closure ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Carbon monoxide undergoes catalytic reactions with unsaturated compounds to give heterocyclic carbonyl compounds. This cyclization has led to new syntheses of imides, lactams, lactones, phthalimidines, indazolones, and tetrahydroquinazolines.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196604351
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Syntheses of Thiocarboxamides (1966)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 5 (1966), S. 447-461 
    Details
    ISSN: 0570-0833
    Keywords: Thiocarboxamides ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Methods for the preparation of thiocarboxamides are described with special reference to progress achieved in the last few years. The discussion is arranged according to the eight most important reaction types.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196604471
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of Isocyanates and Carbodiimides (1966)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 5 (1966), S. 704-712 
    Details
    ISSN: 0570-0833
    Keywords: Isocyanates ; Carbodiimides ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of 1,3-disubstituted ureas and 1-arylsulfonyl-3-alkylureas with phosgene permits the preparation of a number of isocyanates and sulfonyl isocyanates that had not previously been described, or that were difficult to prepare. 1,3-Disubstituted thioureas and 1-aryl-(or alkyl)sulfonyl-3-alkylthioureas give carbodiimides. Thionyl chloride and phosphorus pentachloride react with the urea derivatives in the same way as phosgene. Oxalyl chloride reacts with ureas to form parabanic acid derivatives, whereas with thiourea it gives 2-imino-1,3-thiazolidine-4,5-diones, which can isomerize to parabanic acid derivatives.
    Additional Material: 9 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196607041
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  • 5
    Electronic Resource
    Electronic Resource
    Syntheses of Carboxylic Acids from 1, 1-DichloroehyleneK. Bott, Angew. Chem. 77, 967 (1965); Angew. Chem. internat. Edit. 4, 956 (1965); Chem. Ber., in press.Dedicated to Professor F. Broich on his 60th birthday (1966)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 5 (1966), S. 870-874 
    Details
    ISSN: 0570-0833
    Keywords: Carboxylic acids ; 1,1-Dichloroethylene ; Synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Many β-alkyl- and β-arylpropionic acids are readily obtainable by the reaction of secondary or tertiary alcohols, esters of these, or olefins with the inexpensive 1, 1-dichloroethylene in sulfuric acid. The success of the synthesis depends on the bulk and energy of the carbonium ion intermediate formed from the alcohols or olefins. With carbonium ions having one H atom attached to the carbonium C atom, electrophilic substitution of the 1,1-dichloroethylene takes place to a small extent. Dicarboxylic acids and carboxylic acids with higher molecular weights are sometimes formed as a result of side reactions.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.196608701
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