Syntheses of pseudoceramines A-D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges
2012 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 10, no 6, 1246-1254 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
Royal Society of Chemistry, 2012. Vol. 10, no 6, 1246-1254 p.
IdentifiersURN: urn:nbn:se:umu:diva-52302DOI: 10.1039/c1ob06722bISI: 000299342200016PubMedID: 22179542OAI: oai:DiVA.org:umu-52302DiVA: diva2:503901