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Page 1
Enantiopure Indolo[2,3-a]quinolizidines: Synthesis and Evaluation as NMDA Receptor Antagonists.
Pereira NA, et al. Molecules 2016. PMID 27509489 Free PMC article.
In this communication, we report the development of a small library of indolo[2,3-a]quinolizidines and evaluation of their activity as N-Methyl d-Aspartate (NMDA) receptor antagonists. ...The synthesized enantiopure indolo[2,3-a]quinolizidines were evaluated as NMDA receptor antagonists and one compound was identified to be 2.9-fold more potent as NMDA receptor blocker than amantadine (used in the clinic for Parkinson's disease). ...
In this communication, we report the development of a small library of indolo[2,3-a]quinolizidines and evaluation of their activity a …
Synthesis of polyhydroxylated quinolizidines and azaspiro[4.5]decanes from D-xylose.
Malik M, et al. Org Lett 2013. PMID 24215181
The synthesis of novel polyhydroxylated quinolizidines and azaspiro[4.5]decanes is reported. A key step of this transformation involved an addition of allylmagnesium bromide to an ω-bromonitrile derived from D-xylose followed by an intramolecular displacement of a bromide. ...
The synthesis of novel polyhydroxylated quinolizidines and azaspiro[4.5]decanes is reported. A key step of this transformation …
A convergent stereoselective synthesis of quinolizidines and indolizidines: chemoselective coupling of 2-hydroxymethyl-substituted allylic silanes with imines.
Yang D and Micalizio GC. J Am Chem Soc 2009. PMID 19950989 Free PMC article.
A convergent synthesis of stereodefined indolizidines and quinolizidines through chemoselective allyl transfer between 2-hydroxymethyl-substituted allylic silanes and imines is described. ...
A convergent synthesis of stereodefined indolizidines and quinolizidines through chemoselective allyl transfer between 2-hydro …
Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.
Veerasamy N, et al. J Org Chem 2013. PMID 23627426 Free PMC article.
The total synthesis of cermizine D has been achieved through use of an organocatalyzed, heteroatom Michael addition to access a common intermediate. ...
The total synthesis of cermizine D has been achieved through use of an organocatalyzed, heteroatom Michael addition to access a commo …
Synthesis and glycosidase-inhibitory activity of novel polyhydroxylated quinolizidines derived from D-glycals.
Kumari N and Vankar YD. Org Biomol Chem 2009. PMID 19421448
A number of structurally novel polyhydroxylated quinolizidines have been prepared starting from 2-deoxyglycosylamines which in turn were derived from D-glycals by following a methodology developed in our laboratory. ...
A number of structurally novel polyhydroxylated quinolizidines have been prepared starting from 2-deoxyglycosylamines which in turn w …
Synthesis of highly oxidized quinolizidine via reduction of acylpyridinium cations, and total syntheses of quinolizidines 207I and 1-epi-207I.
Tsukano C, et al. Org Lett 2012. PMID 22440132
A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several functional groups, including carbonyl, silyl, and acetal, were tolerated under mild reaction conditions. The reaction was successfully extended to a one-pot synthesis of a bicyclic compound, and the synthetic strategy was applied to concise total syntheses of quinolizidines 207I and 1-epi-207I, without protecting groups....
A new strategy for synthesizing quinolizidine skeletons by reductive cyclization via acylpyridinium cations was developed. Several fu …
Pd(0)-catalyzed tandem deprotection/cyclization of tetrahydro-β-carbolines on allenes: application to the synthesis of indolo[2,3-a]quinolizidines.
Gobé V and Guinchard X. Org Lett 2014. PMID 24661091
This reaction results in the synthesis of various chiral indolic tetracycles (mainly indolo[2,3a]quinolizidine derivatives) presenting a vinyl function....
This reaction results in the synthesis of various chiral indolic tetracycles (mainly indolo[2,3a]quinolizidine derivatives) pr …
Oxidative Asymmetric Formal Aza-Diels⁻Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones.
Wu X, et al. Molecules 2018. PMID 30200483 Free PMC article.
Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels⁻Alder reaction for enantio- and diastereoselective synthesis of indoloquinolizidine-2-ones from tetrahydro-β-carbolines and α,β-unsaturated ketones is described. The reaction proceeds via tandem ruthenium-catalyzed amine dehydrogenation using tert-butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea-catalyzed formal aza-[4 + 2] cycloaddition, providing a step-economical strategy for the synthesis of these valuable heterocyclic products....
Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels⁻Alder reaction for enantio- and diastereoselective synthesis of …
Synthesis of fused bicyclic systems with nitrogen atom at the bridgehead, including indolizidines and quinolizidines.
Pepe A, et al. J Org Chem 2011. PMID 21452823
Monocyclic as well as fused bicyclic systems with a nitrogen 10 atom at the bridgehead, including indolizidines and quinolizidines, can be prepared in four steps from N-Boc β-lactams. These easily prepared, highly robust, and flexible building blocks allow the incorporation of chirality and structural diversity, rendering the method feasible for diversity- as well as target-oriented synthesis....
Monocyclic as well as fused bicyclic systems with a nitrogen 10 atom at the bridgehead, including indolizidines and quinolizidines, c …
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