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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Biological Products / chemical synthesis*
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Biological Products / chemistry
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Biological Products / isolation & purification
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Molecular Structure
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Porifera / chemistry*
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Spermine / analogs & derivatives*
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Spermine / chemical synthesis
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Spermine / chemistry
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Spermine / isolation & purification
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Stereoisomerism
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Tyrosine / analogs & derivatives*
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Tyrosine / chemical synthesis
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Tyrosine / chemistry
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Tyrosine / isolation & purification
Substances
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Biological Products
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bromotyrosine
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pseudoceramine A
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pseudoceramine B
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spermatinamine
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Spermine
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Tyrosine