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Syntheses of pseudoceramines A-D and a new synthesis of spermatinamine, bromotyrosine natural products from marine sponges
Umeå University, Faculty of Science and Technology, Department of Chemistry. (Centre for Microbial Research)
Umeå University, Faculty of Science and Technology, Department of Chemistry. (Centre for Microbial Research)
Umeå University, Faculty of Science and Technology, Department of Chemistry. (Laboratory for Chemical Bilogy, Centter for Microbial Research, Lab of Molecular Infection Medicine)
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
Abstract [en]

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.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-52302DOI: 10.1039/c1ob06722bISI: 000299342200016PubMedID: 22179542OAI: oai:DiVA.org:umu-52302DiVA: diva2:503901
Available from: 2012-02-17 Created: 2012-02-17 Last updated: 2017-12-07Bibliographically approved

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Hillgren, J MikaelÖberg, Christopher TElofsson, Mikael

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