Synthesis of 2,4,6-trisubstituted chiral piperidines and (-)-dendroprimine by one-pot asymmetric azaelectrocyclization protocol.
[reaction: see text] Stereocontrolled synthesis of 2,4,6-trisubstituted piperidine diastereomers has been realized from common intermediates, obtained by a one-pot azaelectrocyclization protocol. Based on the method, the asymmetric synthesis of an indolizidine alkaloid, (-)-dendroprimine, was achieved.
Kobayashi
Toyoharu
T
School of Science and Technology, Kwansei Gakuin University, Gakuen 2-1, Sanda, Hyogo 669-1337, Japan.
Hasegawa
Futoshi
F
Tanaka
Katsunori
K
Katsumura
Shigeo
S
D000470:Alkaloids / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D007212:Indolizines; D010880:Piperidines; C488243:dendroprimine