Stereoselective synthesis of 2,6-disubstituted piperidines using the iridium-catalyzed allylic cyclization as configurational switch: asymmetric total synthesis of (+)-241 d and related piperidine alkaloids.
Pressing the configurational switch: Use of enantiomeric Ir catalysts allows the vinylpiperidine building blocks 2 a and 2 b to be synthesized with high selectivity. Total syntheses of the dendrobate alkaloid (+)-241 D, its C6-epimer, and a spruce alkaloid are presented as applications.
Gnamm
Christian
C
Organisch-Chemisches Institut der Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Krauter
Caroline M
CM
Brödner
Kerstin
K
Helmchen
Günter
G
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007495:Iridium / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C413204:241D dendrobate alkaloid; D000470:Alkaloids; D010880:Piperidines; D007495:Iridium