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  • Synthesis of the fungal natural product (-)-xylariamide A

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    Author(s)
    Davis, RA
    Kotiw, M
    Griffith University Author(s)
    Davis, Rohan A.
    Year published
    2005
    Metadata
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    Abstract
    The first synthesis of the fungal natural product (-)-xylariamide A 1 is reported. N,O-Bis(trimethylsilyl)acetamide induced coupling of D-tyrosine with (E)-but-2-enedioic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester 5 produced the dechloro natural product 6, which was subsequently monochlorinated using oxone and KCl to yield synthetic 1. (-)-Xylariamide A 1, (+)-xylariamide A 2 and (-)-dechloroxylariamide A 6 displayed no cytotoxic or antimicrobial activity.The first synthesis of the fungal natural product (-)-xylariamide A 1 is reported. N,O-Bis(trimethylsilyl)acetamide induced coupling of D-tyrosine with (E)-but-2-enedioic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester 5 produced the dechloro natural product 6, which was subsequently monochlorinated using oxone and KCl to yield synthetic 1. (-)-Xylariamide A 1, (+)-xylariamide A 2 and (-)-dechloroxylariamide A 6 displayed no cytotoxic or antimicrobial activity.
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    Journal Title
    Tetrahedron Letters
    Volume
    46
    Publisher URI
    http://www.sciencedirect.com/science/journal/00404039
    DOI
    https://doi.org/10.1016/j.tetlet.2005.05.114
    Copyright Statement
    © 2005 Elsevier : Reproduced in accordance with the copyright policy of the publisher : This journal is available online - use hypertext links. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher.
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/4981
    Collection
    • Journal articles

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