Dysiherbaine

The indium-mediated allylation reaction in aqueous media has been applied to the studies on the total synthesis of dysiherbaine (Scheme 8.18).159... 

Dysiherbaine, 162, is a biologically active compound containing the hexahydro-2/7-furo[3,2- ]pyran core. Compound 162 acts as a selective agonist of non-NMDA-type glutamate receptors in the central nervous system <20030BC772, 2003SL993>. 

Dysiherbaine Dysidea herbacea Agonist for non-NMDA type glutamate receptors... 

Sakai R, Kamiya H, Murata M, Shimamoto K. Dysiherbaine a new neurotoxic amino acid from the Micronesian marine sponge Dysidea herbacea. J. Am. Chem. Soc. 1997 119 4112-4116. 

Sasaki, M, Koike, T, Sakai, R, Tachibana, K, Total synthesis of (—)-dysiherbaine, a novel neuroexcitotoxic amino acid. Tetrahedron Lett., 41, 3923-3926, 2000. 

The potent neurotoxin (-)-dysiherbaine was synthesized by S. Flatekayama et al. who assembled the central pyran ring via an intramolecular Michael addition of a primary alcohol to an a, 3-unsaturated ester. The sole product of this key cyclization was a tricyclic lactone, which was isolated in good yield. 

A novel neuroexcitotoxic amino acid, (-)-dysiherbaine, was synthesized starting from a carbohydrate precursor in the laboratory of M. Sasaki.Under benzylation conditions, the cyclic 2,3-epoxy alcohol underwent a facile Payne rearrangement and the rearranged alkoxide was trapped with benzyl bromide. 

Cohen, J. L., Limon, A., Miledi, R., Chamberlin, A. R. Design, synthesis, and biological evaluation of a scaffold for iGluR ligands based on the structure of (-)-dysiherbaine. Bioorg. Med. ChettL Lett. 2006, 16, 2189-2194. 

Total synthesis of dysiherbaine and neodysiherbaine (amino acids of marine origin with pyranofuran core) 13RCA12466. 

In a formal synthesis of the excitatory amino acids dysiherbaine and neodysi-herbaine, oxanorbornene 57 was subjected to a domino RRM/CM process with vinyl acetate using the phosphine-free catalyst 4 (Scheme 2.22) [13g]. The heterobicycHc product 58 was obtained in excellent yield with high ( )-selectivity in the CM event. 

The natural products dysiherbaine (131) and neodysiherbaine A (132), kainate receptor... 

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