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  • Organic Chemistry  (4)
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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: Synthesis of the Lycopodium Alkaloid (±)-Acetylflabellidine via 1,3-Annulation Reactions of EniminesThe 1,3-annulation reaction of 2,3,4,5-tetrahydro-6-methylpyridine (11) with the enimine 7 catalyzed by perchloric acid and subsequent acetylation stereoselectively yield the tetracyclic adduct 2 as the main product, the structure and relative configuration of which are in agreement with the acetyl derivative of the Lycopodium alkaloid flabellidine (1).
    Notes: Die durch Perchlorsäure katalysierte 1,3-Anellierung von 2,3,4,5-Tetrahydro-6-methylpyridin (11) an das Enimin 7 mit anschließender Acetylierung liefert in stereoselektiver Reaktion als Hauptprodukt das tetracyclische Addukt 2, dessen Struktur und relative Konfiguration mit dem Acetylderivat des Lycopodium-Alkaloids Flabellidin (1) identisch ist.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1519-1528 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of the Lycopodium Alkaloid rac-Luciduline from Hexahydro-7-methylquinolineThe 1,4 addition of malonic acid to the eneimine functional group of 2 leads to diastereomeric imines which via disproportionation can be transformed into the pyridine derivative 9. From 9 the ester 5b is obtained stereoselectively. Oxidation of 5b with potassium permanganate and crown ether yields the lactam ester 15. The cyclization and transformation of 15 into rac-luciduline (1) is described. 5b can also be obtained in a simple, nonstereoselective synthesis from the ketone 10.
    Notes: Durch 1,4-Addition von Malonsäure an die Eniminfunktion in 2 entstehen diastereomere Imine, die sich durch Disproportionierung in das Pyridinderivat 9 umwandeln lassen. Stereoselektiv wird daraus der Ester 5b gewonnen, der mit Kaliumpermanganat und Kronenether den Lactamester 15 liefert. Die Cyclisierung und Umwandlung von 15 zum rac-Lucidulin (1) ist beschrieben. Der Ester 5b wird in einer einfachen, nicht stereoselektiven Synthese auch aus dem Keton 10 erhalten.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 220-225 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of the Lycopodium-Alkaloids rac-α-Obscurin through 1,3-Anullation of an EnimineAcid catalysed 1,3-annulation of 1,2,3,4-tetrahydro-6-methyl-2-oxopyridine (1) to the enimine 3, followed by methylation, provides a new regio and stereoselective route to rac-α-obscurine (5). Reduction of rac-N-demethyl-α-obscurine with LiAlH4 yields rac-lycodine (11) and rac-deacetyl-flabellidine (9). A new pathway for the biogenesis of the β-amino-imine 9 is suggested.
    Notes: Die säurekatalysierte 1,3-Anellierung von 1,2,3,4-Tetrahydro-6-methyl-2-oxopyridin (1) an das Enimin 3 liefert nach anschließender Methylierung regio- und stereoselektiv rac-α-Obscurin (5). Reduktion von rac-N-Desmethyl-α-obscurin (4) mit Lithiumaluminiumhydrid führt zur Bildung von rac-Lycodin (11) und rac-Desacetylflabellidin (9). Für das β-Amino-Imin 9 wird ein neuer Biogeneseweg vorgeschlagen.
    Additional Material: 1 Tab.
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 1700-1705 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A Further Synthesis of (±)-LycopodinThe synthesis of (±)-lycopodin from 2-cyanoethyl-5-methyl-1,3-cyclohexanedione (2b) in six steps is described. An important step is the stereoselective 1,3-annulation reaction of the unsaturated imine 4b with acetone dicarboxylic acid yielding the tricyclic ketone 5b.
    Notes: Die Synthese von (±)-Lycopodin (1) aus 2-Cyanethyl-5-methyl-1,3-cylohexandion (2b) in sechs Stufen wird beschrieben. Ein wichtiger Syntheseschritt ist die stereoselektive 1,3-Anellierung des ungesättigten Imins 4b mit Acetondicarbonsäure zum tricyclischen Keton 5b.
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