586347-03-7Relevant academic research and scientific papers
A general strategy for the catalytic, highly enantio- and diastereoselective synthesis of indolizidine-based alkaloids
Abels, Falko,Lindemann, Chris,Schneider, Christoph
, p. 1964 - 1979 (2014/03/21)
Sixteen indolizidine-based alkaloids (IBAs) that were isolated as poison constituents of the skin of frogs were synthesized in a highly flexible and stereoselective manner. As a key step, a three-component, organocatalytic, highly enantio- and diastereose
Straightforward synthesis of indolizidine alkaloid 167B
Gracia, Stéphanie,Jerpan, Rudolf,Pellet-Rostaing, Stéphane,Popowycz, Florence,Lemaire, Marc
experimental part, p. 6290 - 6293 (2011/01/04)
The synthetic access to indolizidines, substituted in C-5 position, was reported with good diastereoselectivity. The strategy developed was based on a key step of Michael addition associated with a Clauson-Kaas condensation.
Novel synthesis of indolizidines and quinolizidines
Tehrani, Kourosch Abbaspour,D'hooghe, Matthias,De Kimpe, Norbert
, p. 3099 - 3108 (2007/10/03)
A very short synthesis of indolizidines, quinolizidines and some higher homologues was developed by alkylation of 2-methyl-1-pyrroline or 6-methyl-2,3,4,5-tetrahydropyridine with 1,3- or 1,4-dihaloalkanes, followed by reduction of the intermediate iminium salts, resulting in the desired 1-azabicyclo[m.n.0]alkanes in good yields.
Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam
Amat, Mercedes,Llor, Nuria,Hidalgo, Jose,Escolano, Carmen,Bosch, Joan
, p. 1919 - 1928 (2007/10/03)
Starting from a common lactam, (3R,8aS)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine (1), or its enantiomer, the enantioselective synthesis of 2-alkylpiperidines and cis- and trans-2,6-dialkylpiperidines is reported. The potential of this approach is illustrated by the synthesis of the piperidine alkaloids (R)-coniine, (2R,6S)-dihydropinidine, (2R,6R)-lupetidine, and (2R,6R)-solenopsin A, the indolizidine alkaloids (5R,8aR)-indolizidine 167B and (3R,5S,8aS)-monomorine I, and the nonnatural base (4R,9aS)-4-methylquinolizidine.
Stereocontrolled alkylation of chiral pyridinium salt toward a short enantioselective access to 2-alkyl- and 2,6-dialkyl-1,2,5,6- tetrahydropyridines
Guilloteau-Bertin, Berangere,Compere, Delphine,Gil, Laurent,Marazano, Christian,Das, Bhupesh C.
, p. 1391 - 1399 (2007/10/03)
Treatment of salts 1a-b with Grignard reagents gives, after reduction of the resulting unstable dihydropyridines 7, the tetrahydropyridines 8a-c, with modest selectivities but in very few steps and under practical conditions. Higher stereo and regioselectivities are obtained with salt 1c which gives the tetrahydropyridines 15a-e. In addition, the dihydropyridine intermediates 11b cyclize to give the new oxazolidine derivatives 12a-e, which turn out to be good precursors of the 2,6-trans-disubstituted tetrahydropyridines 21a-e. Selective syntheses of (-)-lupetidin, (+)-solenopsin, and indolizidines (-)-5 and (-)-6 are presented as representative examples of applications.
Intramolecular schmidt reactions of azides with carbocations: Synthesis of bridged-bicyclic and fused-bicyclic tertiary amines
Pearson, William H.,Walavalkar, Rajesh,Schkeryantz, Jeffrey M.,Fang, Wen-Kui,Blickensdorf, James D.
, p. 10183 - 10194 (2007/10/02)
Aliphatic azides were captured intramolecularly by carbocations, producing aminodiazonium ion intermediates. Carbon-to-nitrogen rearrangement then occurred, generating bridged- or fused-bicyclic α-amino carbocations or iminium ions, depending on the geome
Enantioselective Total Syntheses of Indolizidine Alkaloids 167B and 209D
Polniaszek, Richard P.,Belmont, Stephen E.
, p. 4688 - 4693 (2007/10/02)
Enantioselective total syntheses of the indolizidine alkaloids 167B and 209D are described.The sytheses proceed via a common late-stage intermediate, amino nitrile 8.Each alkaloid was prepared in 10 steps and approximately 23percent overall yield from (S)
