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  • 1
    Electronic Resource
    Electronic Resource
    Total syntheses of the slime mold alkaloid arcyriacyanin APigments from Fungi, Part 67; Part 66: G. Mayer, G. Wille, W. Steglich, Tetrahedron Lett.1996, 26, 4483-4486. (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 70-74 
    Details
    ISSN: 0947-6539
    Keywords: alkaloids ; Heck reactions ; heterocycles ; indoles ; total syntheses ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Arcyriacyanin A (1) has been synthesized by three different routes. In the first synthesis the bisbromomagnesium salt of 2,4′-biindole (5) was treated with dibromomaleimide (6) to yield arcyriacyanin A (1). The second approach used an intramolecular Heck reaction for the cyclization of a 4-(triflyloxy)arcyriarubin 8 to N-methylarcyriacyanin A (2). Thirdly, compound 2 was obtained by a domino Heck reaction between 3-bromo-4-[1-(tert-butoxycarbonyl)indol-3-yl]-1-methylmaleimide (9) and 4-bromoindole (10). The N-methyl derivative 2 could be transformed into arcyriacyanin A (1) by standard methods.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030112
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  • 2
    Electronic Resource
    Electronic Resource
    Pilzfarbstoffe, 60 Über Leucomentine, farblose Vorstufen des Atromentins aus dem Samtfußkrempling (Paxillus atrotomentosus) (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 797-801 
    Details
    ISSN: 0170-2041
    Keywords: Terphenyl derivatives ; Leucomentins ; 2-Hexenoic acid, 4,5-epoxy- ; Paxillus atrotomentosus ; Atromentin, precursor of ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Fungal Pigments, 60. - Leucomentins, Colourless Precursors of Atromentin from the Mushroom Paxillus atrotomentosusAtromentin (1) occurs in sporophores of Paxillus atrotomentosus mainly in form of the colourless leucomentins 3-5. These compounds constitute esters of leucoatromentin with (2Z,4S,5S)-4,5-epoxy-2-hexenoic acid. The absolute configuration of the latter has been determined by its conversion into (+)-O-acetylosmundalactone (6a). The mechanism of the acid-catalyzed cleavage of the acyl residues has been studied by means of 18O labeling.
    Notes: Atromentin (1) liegt in Fruchtkörpern des Samtfußkremplings hauptsächlich in Form der farblosen Leucomentine 3-5 vor. Die Leucomentine sind Ester des Leukoatromentins mit (2Z,4S,5S)-4,5-Epoxy-2-hexensäure, deren absolute Konfiguration durch Überführung in (+)-O-Acetylosmundalacton (6a) bestimmt werden konnte. Dabei wurde der Mechanismus der säurekatalysierten Abspaltung der Säurereste durch 18O-Markierung aufgeklärt.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890227
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  • 3
    Electronic Resource
    Electronic Resource
    Pilzfarbstoffe, 61 Flavomentine und Spiromentine, neue Terphenylchinon-Derivate aus Paxillus atrotomentosus und P. panuoides (Boletales) (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 803-810 
    Details
    ISSN: 0170-2041
    Keywords: Fungal pigments ; Terphenylquinones ; Flavomentins ; Spiromentins ; Paxillus atrotomentosus ; Paxillus panuoides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Fungal Pigments, 61. - Flavomentins and Spiromentins, Novel Terphenylquinone Derivatives from Paxillus atrotomentosus and P. panuoides (Boletales)The gilled toadstools Paxillus atrotomentosus and P. panuoides produce small amounts of orange-yellow flavomentins and violet spiromentins. The flavomentins 1-3 constitute mono- and diesters of atromentin (6) with (2Z,4E)-2,4-hexadienoic acid or (2Z,4S,5S)-4,5-epoxy-2-hexenoic acid. In addition, 3-O-acetylatromentin (4) has been isolated from P. atrotomentosu. The spiromentins 8,11,12, and 13 possess a unique spiro structure in which a 4,5-dihydroxy-1,2-benzoquinone is linked to a lactone acetal unit. The structures of the pigments were confirmed by the synthesis of model compounds and the biomimetic conversion of flavomentin B (2) into the spiromentins B (11) and C (12).
    Notes: Die Kremplinge Paxillus atrotomentosus und P. panuoides produzieren in geringen Mengen orangegelbe Flavomentine und violette Spiromentine. Bei den Flavomentinen 1-3 handelt es sich um Ester des Atromentins (6) mit (2Z,4E)-2,4-Hexadiensäure oder (2Z,4S,5S)-4,5-Epoxy-2-hexensäure, außerdem kommt als weitere Verbindung dieses Typs 3-O-Acetylatromentin (4) vor. Die Spiromentine 8, 11, 12 und 13 besitzen eine ungewöhnliche Spirostruktur, in der ein 4,5-Dihydroxy-1,2-benzochinon mit einem Lacton acetalartig verknüpft ist. Die spektroskopisch abgeleiteten Strukturen der Farbstoffe konnten durch die Synthese von Modellverbindungen und die biomimetische Überführung von Flavomentin B (2) in die Spiromentine B (11) und C (12) gesichert werden.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890228
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  • 4
    Electronic Resource
    Electronic Resource
    Biomimetic Synthesis of Lamellarin G. Trimethyl EtherAlkaloids from Marine Organisms, Part 2. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. Part 1: ref. [3]. (1997)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 36 (1997), S. 155-156 
    Details
    ISSN: 0570-0833
    Keywords: alkaloids ; arenes ; Heck reactions ; natural products ; synthetic methods ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.199701551
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