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  • A microwave-assisted stereoselective synthesis of polyandrocarpamines A and B

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    Author(s)
    Davis, Rohan A
    Baron, Paul S
    Neve, Juliette E
    Cullinane, Carleen
    Griffith University Author(s)
    Davis, Rohan A.
    Year published
    2009
    Metadata
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    Abstract
    A stereoselective synthesis of the marine natural products, polyandrocarpamines A and B, has been achieved using a high-yielding one-step aldol condensation reaction under microwave conditions. The structures of both synthetic compounds were confirmed following 1D and 2D NMR, UV, IR and MS spectral analysis, and by comparison with literature data. Both synthetic natural products were assigned Z geometry about their exocyclic double bond on the basis of 13C/1H long-range coupling constants, which were measured using a gHSQMBC experiment. Polyandrocarpamines A and B were evaluated for their cytotoxicity towards the tumour cell ...
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    A stereoselective synthesis of the marine natural products, polyandrocarpamines A and B, has been achieved using a high-yielding one-step aldol condensation reaction under microwave conditions. The structures of both synthetic compounds were confirmed following 1D and 2D NMR, UV, IR and MS spectral analysis, and by comparison with literature data. Both synthetic natural products were assigned Z geometry about their exocyclic double bond on the basis of 13C/1H long-range coupling constants, which were measured using a gHSQMBC experiment. Polyandrocarpamines A and B were evaluated for their cytotoxicity towards the tumour cell lines, MCF-7 (breast), H460 (lung) and SF268 (central nervous system). Polyandrocarpamine A displayed selective cytotoxicity towards the SF268 cell line with a GI50 value of 65 卮
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    Journal Title
    Tetrahedron Letters
    Volume
    50
    Issue
    8
    DOI
    https://doi.org/10.1016/j.tetlet.2008.12.010
    Copyright Statement
    © 2009 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
    Subject
    Medicinal and biomolecular chemistry
    Biologically active molecules
    Organic chemistry
    Organic chemical synthesis
    Publication URI
    http://hdl.handle.net/10072/25641
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    • Journal articles

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