Total synthesis of quinolizidine (-)-217A.
We report here the construction of quinolizidine ring systems by intramolecular cyclization of suitable functionalized piperidines via a reductive amination sequence. This reaction proceeds with a total stereocontrol at C4. The preparation of the piperidine precursors is based on a chain elongation of a piperidine aldehyde either by aldolization or by Wittig reaction. We applied this second route to the total synthesis of quinolizidine (-)-217A from (S)-methyl 2-((S)-1-((R)-1-phenylethyl)piperidin-2-yl)propanoate 5.
Fellah
Mouloud
M
UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), C. 43, Equipe Hétérocycle, 4 place Jussieu, 75005 Paris, France.
Santarem
Marco
M
Lhommet
Gérard
G
Mouriès-Mansuy
Virginie
V
D000447:Aldehydes / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D010880:Piperidines; D011807:Quinolizines; C473050:alkaloid 217A; C032727:piperidine