Very short and efficient syntheses of the spermine alkaloid kukoamine A and analogs using isolable succinimidyl cinnamates

Thomas Garnelis, Constantinos M. Athanassopoulos, Dionissios Papaioannou (Lead / Corresponding author), Ian M. Eggleston, Alan H. Fairlamb

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    Direct selective acylation of the primary amino functions of spermine and spermidine with a variety of isolable succinimidyl cinnamates, followed by catalytic hydrogenation, gave high yields of the spermine alkaloid kukoamine A and analogs suitable for structure-activity relationship studies. Suitable succinimidyl cinnamates were readily obtained through Wittig reaction of aromatic aldehydes with the ylides Ph3P=CRCO2Me, followed by saponification and activation with N-hydroxysuccinimide in the presence of N,N'-dicyclohexylcarbodiimide.

    Original languageEnglish
    Pages (from-to)264-265
    Number of pages2
    JournalChemistry Letters
    Volume34
    Issue number2
    DOIs
    Publication statusPublished - 5 Feb 2005

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    Cinnamates
    Spermine
    Alkaloids
    Dicyclohexylcarbodiimide
    Saponification
    Acylation
    Spermidine
    Aldehydes
    Hydrogenation
    Chemical activation
    kukoamine A

    Cite this

    Garnelis, Thomas ; Athanassopoulos, Constantinos M. ; Papaioannou, Dionissios ; Eggleston, Ian M. ; Fairlamb, Alan H. / Very short and efficient syntheses of the spermine alkaloid kukoamine A and analogs using isolable succinimidyl cinnamates. In: Chemistry Letters. 2005 ; Vol. 34, No. 2. pp. 264-265.
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    Very short and efficient syntheses of the spermine alkaloid kukoamine A and analogs using isolable succinimidyl cinnamates. / Garnelis, Thomas; Athanassopoulos, Constantinos M.; Papaioannou, Dionissios (Lead / Corresponding author); Eggleston, Ian M.; Fairlamb, Alan H.

    In: Chemistry Letters, Vol. 34, No. 2, 05.02.2005, p. 264-265.

    Research output: Contribution to journalArticle

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