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

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Hillgren JM, Oberg CT, Elofsson M

Org. Biomol. Chem. 10 (6) 1246-1254 [2012-02-14; online 2011-12-20]

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.

Chemical Biology Consortium Sweden (CBCS) [Collaborative]

PubMed 22179542

DOI 10.1039/c1ob06722b

Crossref 10.1039/c1ob06722b

Laboratories for Chemical Biology Umeå (LCBU)