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Issue 6, 2012
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Syntheses of pseudoceramines A–D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges

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Abstract

Herein we report the total syntheses of pseudoceramine A-D (2–5) and spermatinamine (1) isolated from the marine sponge Pseudoceratina sp. Direct acyl substitution of α-hydroxyiminoesters with amine nucleophiles was developed as a key transformation. The synthetic compounds confirm the reported structures and importantly gives access to non-symmetrical spermine based natural products carrying two different bromotyrosine building blocks. Our new synthesis of spermatinamine is two steps shorter and more efficient than the previously reported sequence.

Graphical abstract: Syntheses of pseudoceramines A–D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges

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The article was received on 12 Oct 2011, accepted on 15 Nov 2011 and first published on 16 Nov 2011


Article type: Paper
DOI: 10.1039/C1OB06722B
Citation: Org. Biomol. Chem., 2012,10, 1246-1254

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    Syntheses of pseudoceramines A–D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges

    J. M. Hillgren, C. T. Öberg and M. Elofsson, Org. Biomol. Chem., 2012, 10, 1246
    DOI: 10.1039/C1OB06722B

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