An efficient synthesis of semiplenamide C

An efficient synthesis of semiplenamide C

Semiplenamides are anandamide-like fatty acid amide metabolites previously isolated from a marine cyanobacterium that display a range of biological activity. Novel syn-aldol/dehydration methodology has been developed for the stereoselective synthesis of the core ( E)-α,β-unsaturated amide functional...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 46; no. 33; pp. 5547 - 5549
Main Authors: Davies, Iwan R., Cheeseman, Matt, Niyadurupola, D. Gangani, Bull, Steven D.
Format: Journal Article
Language:English
Published: Elsevier Ltd 15-08-2005
Subjects:
Elimination
N-Acyl-oxazolidin-2-one
Natural product
syn-Aldol
Natural product
N-Acyl-oxazolidin-2-one
syn-Aldol
Elimination
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Summary:Semiplenamides are anandamide-like fatty acid amide metabolites previously isolated from a marine cyanobacterium that display a range of biological activity. Novel syn-aldol/dehydration methodology has been developed for the stereoselective synthesis of the core ( E)-α,β-unsaturated amide functionality of this class of natural product, and employed for the efficient synthesis of semiplenamide C.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.06.027