Journal ArticleDOI
Epibatidine: a novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an ecuadoran poison frog
Thomas F. Spande,H. M. Garraffo,M. W. Edwards,Herman J. C. Yeh,Lewis K. Pannell,John W. Daly +5 more
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TLDR
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane represents a unique new class of alkaloids.Abstract:
A potent non-opioid analgesic, epibatidine, has been isolated from skins of the Ecuadoran poison frog, Epipedobates tricolor, and its structure determined by MS, IR, and 1 H NMR analyses as exo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptane. It represents a unique new class of alkaloidsread more
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Innovation im Pflanzenschutz: Trends in der Forschung
Jörg Dr. Stetter,Folker Lieb +1 more
TL;DR: Aufsatz spannt den Bogen von den Anfangen des chemischen Pflanzenschutzes bis in die Gegenwart and will aufzeigen, wie sich die industrielle Pflanschutzforschung auf die aktuellen and zukunftigen Herausforderungen einstellt.
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Synthesis of constrained prolines by Diels–Alder reaction using a chiral unsaturated oxazolone derived from (R)-glyceraldehyde as starting material
TL;DR: In this article, a new route for the asymmetric synthesis of enantiomerically pure 2-substituted 7-azabicyclo[2.2.1]heptane-1-carboxylic acids was described.
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Synthesis of endo-2-phenyl-7-azabicyclo[2.2.1]heptane via high pressure Diels-Alder reactions of pyrroles
TL;DR: In this paper, a straightforward route to racemic endo-2-phenyl-7-azabicyclo[2.2.1]heptane (an analogue of epibatidine) is described via the high pressure Diels-Alder reaction of 1-methoxycarbonyl-3phenylthio-pyrrole with phenyl vinyl sulphone.
Journal ArticleDOI
Chemoenzymatic formal synthesis of (-)- and (+)-epibatidine
Derek R. Boyd,Narain D. Sharma,Magdalena Kaik,Peter B. A. McIntyre,Paul J. Stevenson,Christopher C. R. Allen +5 more
TL;DR: The cis-dihydrocatechol, derived from enzymatic cis- dihydroxylation of bromobenzene using the microorganism Pseudomonas putida UV4, was converted into (-)-epibatidine in eleven steps with complete stereocontrol.
Journal ArticleDOI
Synthesis of chiral 2-(2′-pyrrolidinyl)pyridines from (S)- and (R)-proline: potential ligands of the neuronal nicotinic acetylcholine receptors
TL;DR: A new strategy for a straightforward synthesis of novel optically active nicotine analogues starting from ( S- and ( R )-proline is reported utilizing as the key steps the inverse electron demand Diels–Alder reaction of chiral 5-(2′-pyrrolidinyl)-1,2,4-triazines.