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  • 1
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reaction of Acyclic Imides with 1-Elhoxycarbonylcyclopropyltriphenylphosphonium Tetrafluoroborate: An Easy Route to 1H-Pyrrole-3-carboxylatesThe reaction of anions of the acyclic imides 1 with the cyclopropylphosphonium salt 2 yields ethyl 1-acyl-Δ2-pyrroline-3-carboxylates 3, substituted in position 2, which can be dehydrogenated to yield the corresponding 1-acylpyrroles 4 and subsequently deacylated to give the pyrroles 5. The scope of the reaction is discussed.
    Notes: Durch Umsetzung der Anionen offenkettiger Imide 1 mit dem Cyclopropylphosphoniumsalz 2 werden 2-substituierte 1-Acyl-Δ2-pyrrolin-3-carbonsäure-ethylester 3 erhalten, die zu den entsprechenden 1-acylierten 3-Pyrrolcarbonsäureestern 4 dehydriert und anschließend zu Pyrrolen 5 de-acyliert werden. Die Anwendungsbreite der Reaktionsfolge wird beschrieben.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reaction of Cyclic Imides with 1-Ethoxycarbonylcyclopropyltriphenylphosphonium Tetrafluoroborate: A Simple Diastereoselective Route to (±)-IsoretronecanolBicyclic N-bridgehead lactams 2 and 3 are obtained by reacting the anions of succinimide and glutarimide with the cyclopropylphosphonium salt 1. Starting from 2 a diastereoselective synthesis of (±)-isoretronecanol (7) is achieved. The adducts 10, which are obtained from monothioimide anions and 1, do not cyclize regioselectively. Dehydrogenation of 2 using N-bromosuccinimide yields the 5,6-dihydropyrrolizine 11; however, reaction with lead tetraacetate gives the isomer 12. Succinimide reacts with the cyclopropylphosphonium salt 13 to give the pyrrolizidine 14.
    Notes: N-Brückenkopfbicyclische Lactame 2 und 3 werden aus den Anionen des Succinimids und Glutarimids mit dem Cyclopropylphosphoniumsalz 1 erhalten. Ausgehend von 2 gelingt eine einfache diastereoselektive Synthese des (±)-Isoretronecanols (7). Die aus Monothioimid-Anionen und 1 gebildeten Adukte 10 sind nicht regioselektiv cyclisierbar. Die Dehydrierung des Tetrahydropyrrolizins 2 zum 5,6-Dihydroderivat 11 gelingt mit N-Bromsuccinimid; mit Bleitetraacetat entsteht hingegen das Isomere 12. Das Cyclopropylphosphoniumsalz 13 reagiert mit dem Anion des Succinimids zum Pyrrolizidin 14.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1413-1421 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Studies on the Synthesis of Mitomycins, 2.- Synthesis of the Mitosene Skeleton by Intramolecular Wittig OlefinationEfficient methods for the preparation of benzopyrrolizine derivatives using intramolecular Wittig olefination as cyclization reaction are presented. Subsequent Vilsmeter formylation results in the formation of the mitosene skeleton.
    Notes: Es werden effiziente Darstellungsmethoden für Benzopyrrolidin-Derivate beschrieben, die eine intramolekulare Wittig-Olefinierung als Cyclisierungsreaktion verwenden. Anschließende Vilsmeier-Reaktion führt zum Mitosen-Gerüst.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1437-1447 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Studies on the Synthesis of Mitomycins, 4.- Elucidation of the Configuration of Mitosane DerivativesThe configurations of the mitosane derivatives described in the previous communications1) were established by spectroscopic investigations and X-ray analysis of rac-1e.
    Notes: Die Konfigurationen der in den vorstehenden Arbeiten beschriebenen Mitosan-Derivate wurden durch spektroskopische Untersuchungen und eine Röntgenstrukturanalyse der Verbindung rac-1e bewiesen.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1398-1412 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Studies on the Synthesis of Mitomycins, 1.- Synthesis of the Mitosane Skeleton by Intramolecular Condensation and Reformatsky ReactionBenzopyrrolizinones 10 were obtained from the succinimido esters 6b, c by intramolecular condensation in moderate yields. A stereoselective Reformatsky reaction of the bromo esters 7 was accelerated by ultrasonication to give the 9a-functionalized mitosane derivatives 8 in high yields.
    Notes: Ausgehend von den Succinimidoestern 6b, c gelingt die Synthese der Benzopyrrolizinone 10 in nur mäßigen Ausbeuten. Eine Reformatskij-Reaktion der Bromester 7 verlief unter Einwirkung von Ultraschall stereoselektiv in hohen Ausbeuten zu den 9a-funktionalisierten Mitosanderivaten 8.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1422-1436 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Studies on the Synthesis of Mitomycins, 3.- Functionalisations of Mitosene DerivativesThe introduction of a (carbamoyloxy)methyl function into position 9 of the benzopyrrolizinones 1 is described together with a stereoselective functionalisations of the 9a position. Possibilities to introduce the quinone group are presented.
    Notes: Es werden Versuche zur Finführung einer (Carbamoyloxy)methyl-Gruppe in Position 9 der Benzopyrrolizinone 1 beschrieben. Anschließend wird über eine stereoselektive Funktionalisierung der 9a-Position und über Möglichkeiten der Einführung der Chinongruppe berichtet.
    Type of Medium: Electronic Resource
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