217499-52-0Relevant articles and documents
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.
Enantioselective synthesis of the trans-2,6-dialkylpiperidine alkaloids (2R,6R)-lupetidine and (2R,6R)-solenopsin A
Amat, Mercedes,Hidalgo, Jose,Llor, Nuria,Bosch, Joan
, p. 2419 - 2422 (2007/10/03)
The enantioselective synthesis of the trans-2,6-dialkylpiperidine alkaloids (2R,6R)-lupetidine and (2R,6R)-solenopsin A from 6-methyl-2- piperidone 1 is described. The key step of this synthesis consists of the addition of a dialkylcopper derivative to the thioimidate salt 3 followed by sodium borohydride reduction of the resulting iminium salt.