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Hydroxymethyl-Branched Polyhydroxylated Indolizidines: Novel Selective α-Glucosidase Inhibitors.
Boisson J, et al. Org Lett 2015. PMID 26181493
α,α-Disubstituted piperidines and conformationally constrained polyhydroxylated indolizidines bearing a hydroxymethyl substituent in position 8a were synthesized from a readily available l-sorbose-derived ketonitrone. ...Subsequent N-allylation and ring-closing metathesis afforded 8a-branched indolizidines in high yield. The newly prepared iminosugars demonstrated highly potent inhibition of α-glucosidases. ...
α,α-Disubstituted piperidines and conformationally constrained polyhydroxylated indolizidines bearing a hydroxymethyl substituent in …
Simple Indolizidine and Quinolizidine Alkaloids.
Michael JP. Alkaloids Chem Biol 2016 - Review. PMID 26777309
This review of simple indolizidine and quinolizidine alkaloids (i.e., those in which the parent bicyclic systems are in general not embedded in polycyclic arrays) is an update of the previous coverage in Volume 55 of this series (2001). ...The penultimate section of the review deals with the sizable group of simple indolizidine and quinolizidine alkaloids isolated from, or detected in, ants, mites, and terrestrial amphibians, and includes an overview of the "dietary hypothesis" for the origin of the amphibian metabolites. ...
This review of simple indolizidine and quinolizidine alkaloids (i.e., those in which the parent bicyclic systems are in general not e …
NHC-mediated cross-coupling of sugar-derived cyclic nitrones with enals: general and efficient synthesis of polyhydroxylated pyrrolizidines and indolizidines.
Xu WY, et al. Org Biomol Chem 2013. PMID 23749268
A general and efficient method for the synthesis of polyhydroxylated pyrrolizidines and indolizidines has been developed based on the NHC-catalyzed cross-coupling of sugar-derived cyclic nitrones with enals, which afforded the key intermediates, γ-hydroxyl amino esters, in good to excellent yields. Thus, a variety of polyhydroxylated pyrrolizidines and indolizidines have been synthesized and assayed against various glycosidases, which showed that aryl or alkyl substituents at C-7 of pyrrolizidines or at C-8 of indolizidines reduced the potency of the glycosidase inhibition of these bicyclic iminosugars....
A general and efficient method for the synthesis of polyhydroxylated pyrrolizidines and indolizidines has been developed based on the …
Enantioselective synthesis of an octahydroindolizine (indolizidine) alcohol using an enzymatic resolution.
Zhang J, et al. Org Biomol Chem 2017. PMID 28291271
The approach uses a Novozym 435-mediated kinetic resolution of racemic octahydroindolizine (indolizidine) alcohol 13 as a key step (up to 100 g scale)....
The approach uses a Novozym 435-mediated kinetic resolution of racemic octahydroindolizine (indolizidine) alcohol 13 as a key step (u …
Synthesis of indolizidines from optically pure α-amino acids via stereocontrolled rhodium-catalyzed hydroformylation of N-allylpyrroles.
Lazzaroni R and Settambolo R. Chirality 2011 - Review. PMID 21858877
Indolizidine alkaloids have attracted considerable attention because of their vast array of structural diversity and varied biological activity. ...The formed pyrrolylbutanals undergo an intramolecular cyclodehydration to 5,6-dihydroindolizines, which are fully hydrogenated to indolizidines. ...
Indolizidine alkaloids have attracted considerable attention because of their vast array of structural diversity and varied biologica
Α,β-unsaturated diazoketones as versatile building blocks for the synthesis of hydroxylated piperidines, indolizidines and quinolizidines.
Bernardim B, et al. Curr Top Med Chem 2013. PMID 23978131
A four-step approach for the synthesis of dihydroxylated piperidine, quinolizidine and indolizidine systems is described employing α,β-unsaturated diazoketones as versatile building blocks. ...
A four-step approach for the synthesis of dihydroxylated piperidine, quinolizidine and indolizidine systems is described employing α, …
Synthesis of functionalized indolizidines through Pauson-Khand cycloaddition of 2-allylpyrrolidines.
McCormack MP and Waters SP. J Org Chem 2013. PMID 23311620 Free PMC article.
A concise entry to functionalized indolizidine scaffolds through a domino 2-aza-Cope-[3 + 2] dipolar cycloaddition and Pauson-Khand [2 + 2 + 1] cyclization has been accomplished. The process was conducted under mild conditions to afford diverse indolizidine systems as single diastereomers in good overall yields....
A concise entry to functionalized indolizidine scaffolds through a domino 2-aza-Cope-[3 + 2] dipolar cycloaddition and Pauson-Khand [ …
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