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

J. Mikael Hillgren; Christopher T. Öberg; Mikael Elofsson

doi:10.1039/C1OB06722B

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

J. Mikael Hillgren,^a Christopher T. Öberg^a and Mikael Elofsson*^b

Author affiliations

* Corresponding authors

^a Umeå Centre for Microbial Research, Department of Chemistry, Umeå University, Umeå, Sweden

^b Laboratories for Chemical Biology Umeå, Umeå Centre for Microbial Research, Laboratories for Molecular Infection Medicine Sweden, Department of Chemistry, Umeå University, Umeå, Sweden
E-mail: mikael.elofsson@chem.umu.se
Tel: +46-90-7869328

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.

Additions and corrections

Publication details

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

Request permissions
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
If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.

For reproduction of material from PCCP:
Reproduced from Ref. XX with permission from the PCCP Owner Societies.

For reproduction of material from PPS:
Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.

For reproduction of material from all other RSC journals and books:
Reproduced from Ref. XX with permission from The Royal Society of Chemistry.
If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

In all cases the Ref. XX is the XXth reference in the list of references.

If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC

For reproduction of material from PCCP:
[Original citation] - Reproduced by permission of the PCCP Owner Societies

For reproduction of material from PPS:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC

For reproduction of material from all other RSC journals:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry
If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Organic & Biomolecular Chemistry

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

Abstract

Supplementary files

Additions and corrections

Publication details

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

Search articles by author

Spotlight

Advertisements