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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 …
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. This article relates the results that we obtained in the field of the total synthesis of indolizidines from α-amino acids, based on the rhodium-catalyzed hydroformylation of N-allylpyrroles intermediates. ...
Indolizidine alkaloids have attracted considerable attention because of their vast array of structural diversity and varied biologica
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 [ …
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 …
Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes.
Lee EE and Rovis T. Org Lett 2008. PMID 18284249 Free PMC article.
An enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters by way of a rhodium-catalyzed [2+2+2] cycloaddition of substituted alkenyl isocyanates and terminal alkynes is described. ...
An enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters by way of a rhodium-catalyzed [2+2 …
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 …
Total synthesis and isolation of citrinalin and cyclopiamine congeners.
Mercado-Marin EV, et al. Nature 2014. PMID 24828190 Free PMC article.
However, the presence of a nitrogen atom in a target molecule can complicate its chemical synthesis because of the basicity of nitrogen atoms and their susceptibility to oxidation. Obtaining such compounds by chemical synthesis can be further complicated by the presence of multiple nitrogen atoms, but it can be done by the selective introduction and removal of functional groups that mitigate basicity. ...
However, the presence of a nitrogen atom in a target molecule can complicate its chemical synthesis because of the basicity of …
Olefin metathesis based approach to diversely functionalized pyrrolizidines and indolizidines; total synthesis of (+)-monomorine.
Lesma G, et al. J Org Chem 2009. PMID 19067565
New scaffolds for the stereoselective synthesis of diversely functionalized chiral enantiopure indolizidines and pyrrolizidines were synthesized from the cross and ring-closing metathesis reactions of appropriate intermediates, readily available from L-pyroglutamic acid. The versatility of this strategy was demonstrated by the synthesis of an indolizidine-based azasugar analogue and of the natural alkaloid (+)-monomorine....
New scaffolds for the stereoselective synthesis of diversely functionalized chiral enantiopure indolizidines and pyrrolizidine …
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