Enantioselective Synthesis of (−)-Dysiherbaine

Dysiherbaine, a natural product isolated from the Marine sponge Dysidea herbacea, has been shown to be a selective agonist of non-NMDA type glutamate receptors, kainate receptors. An enantioselective synthesis of dysiherbaine is reported. Metathesis of the diene followed by conversion of the resulti...

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Veröffentlicht in:	Organic letters 2015-08, Vol.17 (16), p.3972-3974
Hauptverfasser:	Do, Ha, Kang, Chang Won, Cho, Joon Hyung, Gilbertson, Scott R
Format:	Artikel
Sprache:	eng
Schlagworte:	Alanine - analogs & derivatives Alanine - chemical synthesis Alanine - chemistry Alanine - pharmacology Alkenes - chemistry Amino Acids - chemistry Animals Biological Products - chemical synthesis Biological Products - chemistry Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Bridged Bicyclo Compounds, Heterocyclic - pharmacology Marine Biology Molecular Structure Porifera - chemistry Receptors, Glutamate - drug effects Receptors, Kainic Acid - drug effects Stereoisomerism
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creator	Do, Ha Kang, Chang Won Cho, Joon Hyung Gilbertson, Scott R
description	Dysiherbaine, a natural product isolated from the Marine sponge Dysidea herbacea, has been shown to be a selective agonist of non-NMDA type glutamate receptors, kainate receptors. An enantioselective synthesis of dysiherbaine is reported. Metathesis of the diene followed by conversion of the resulting alkene to the amino alcohol and addition of the amino acid provides the natural product. This synthesis differs from previous approaches to the molecule in that the functionality on the tetrahydropyran ring is installed late in the route.
doi_str_mv	10.1021/acs.orglett.5b01821
format	Article
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subjects	Alanine - analogs & derivatives Alanine - chemical synthesis Alanine - chemistry Alanine - pharmacology Alkenes - chemistry Amino Acids - chemistry Animals Biological Products - chemical synthesis Biological Products - chemistry Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Bridged Bicyclo Compounds, Heterocyclic - pharmacology Marine Biology Molecular Structure Porifera - chemistry Receptors, Glutamate - drug effects Receptors, Kainic Acid - drug effects Stereoisomerism
title	Enantioselective Synthesis of (−)-Dysiherbaine
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