163513-99-3Relevant academic research and scientific papers
Pd-catalyzed asymmetric β-hydride elimination en route to chiral allenes
Crouch, Ian T.,Neff, Robynne K.,Frantz, Doug E.
supporting information, p. 4970 - 4973 (2013/06/04)
We wish to report our preliminary results on the discovery and development of a catalytic, asymmetric β-hydride elimination from vinyl Pd(II)-complexes derived from enol triflates to access chiral allenes. To achieve this, we developed a class of chiral p
The enantiomers of epiboxidine and of two related analogs: Synthesis and estimation of their binding affinity at α4β2 and α7 neuronal nicotinic acetylcholine receptors
Dallanoce, Clelia,Matera, Carlo,De Amici, Marco,Rizzi, Luca,Pucci, Luca,Gotti, Cecilia,Clementi, Francesco,De Micheli, Carlo
experimental part, p. 543 - 551 (2012/08/29)
Epiboxidine hydrochlorides (+)-2 and (-)-2, which are the structural analogs of the antipodes of epibatidine (-)-1, as well as the enantiomeric pairs (+)-3/(-)-3 and (+)-4/(-)-4 were synthesized and tested for binding affinity at α4β2 and α7 nicotinic acetylcholine receptor (nAChR) subtypes. Final derivatives were prepared through the condensation of racemic N-Boc-7-azabicyclo[2.2.1]heptane-2-one (±)-5 with the resolving agent (R)-(+)-2-methyl-2-propanesulfinamide. The pharmacological analysis carried out on the three new enantiomeric pairs evidenced an overall negligible degree of enantioselectivity at both nAChRs subtypes, a result similar to that reported for both natural and unnatural epibatidine enantiomers at the same investigated receptor subtypes.
7-AZONIABICYCLO [2.2.1] HEPTANE DERIVATIVES, METHODS OF PRODUCTION, AND PHARMACEUTICAL USES THEREOF
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Page/Page column 41, (2011/08/21)
Muscarinic acetylcholine receptor antagonists and methods of using them for the treatment of muscarinic acetylcholine receptor-mediated diseases, such as pulmonary diseases, are provided.
Efficient resolution of N-Boc-7-azabicyclo[2.2.1]hept-5-en-2-one: Formal syntheses of natural epibatidine and its enantiomer
Moreno-Vargas, Antonio J.,Vogel, Pierre
, p. 3173 - 3176 (2007/10/03)
The efficient resolution of racemic N-Boc-7-azabicyclo[2.2.1]hept-5-en-2- one (±)-2 via aminal formation with (R,R)-1,2-diphenylethylenediamine 4 is reported. Acidic hydrolysis furnishes the enantiomeric ketones (+)-2 and (-)-2 that were transformed into 7-azabicyclo[2.2.1]heptan-2-one (-)-3 and (+)-3. The process constitutes a formal synthesis of (+)- and (-)-epibatidine.
Synthesis of enantiopure analogues of 3-hydroxyproline and derivatives
Avenoza, Alberto,Barriobero, Jose I.,Busto, Jesus H.,Cativiela, Carlos,Peregrina, Jesus M.
, p. 625 - 632 (2007/10/03)
All four enantiomerically pure 2-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, novel restricted analogues of 3-hydroxyproline, are described. The synthesis starts with the Diels-Alder reaction between methyl 2-benzamidoacrylate and Danishefsky's
Synthesis of (+)- and (-)-N-BOC-7-azabicyclo[2.2.1]heptan-2-ones, versatile intermediates for the enantiospecific synthesis of (+)- and (-)-epibatidine and analogues
Hernandez,Marcos,Rapoport
, p. 2683 - 2691 (2007/10/02)
(+)- and (-)-Epibatidine, nonopiate antinociceptive alkaloids, have been prepared from (-)- and (+)-N-BOC-7-azabicyclo[2.2.1]heptan-2-one which were produced by resolution of the racemic mixture of the corresponding alcohols obtained in the previous racemic synthesis. In the present work, we report the enantiospecific synthesis of (-)- and (+)-N-BOC-7-azabicyclo[2.2.1]heptan-2-one from L-glutamic acid and levulinic acid. Also, this report describes the selective formation of trans-2,3-disubstituted-7-azabicyclo[2.2.1]heptanes from N-benzyl-5-(1'-methoxycarbonyl-3'-exobutyl)proline via a decarbonylation/iminium ion cyclization process. These functionalized intermediates are of potential value for the enantiospecific synthesis of epibatidine analogues.
Total Synthesis and Determination of the Absolute Configuration of Epibatidine
Fletcher, Stephen R.,Baker, Raymond,Chambers, Mark S.,Herbert, Richard H.,Hobbs, Sarah C.,et al.
, p. 1771 - 1778 (2007/10/02)
The synthesis of (+)- and (-)-epibatidine (exo-2-(2-chloropyridin-5-yl)-7-azabicycloheptane) via reaction of 5-lithio-2-chloropyridine with (+)- and (-)-N-BOC-7-azabicycloheptan-2-one is described.The absolute configuration of the natural product is shown to be 1R,2R,4S.
