Syntheses of pseudoceramines A-D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges |
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Authors: | Hillgren J Mikael Oberg Christopher T Elofsson Mikael |
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Affiliation: | Ume? Centre for Microbial Research, Department of Chemistry, Ume? University, SE-60187, Ume?, Sweden. |
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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. |
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