A divergent approach to 3-piperidinols: a concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton.
Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine of utility in target-directed synthesis is reported.
School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand.
Glenn
G
Archibald
Chih-Pei
CP
Lin
Peter
P
Boyd
David
D
Barker
Vittorio
V
Caprio
D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D054837:Quinolizidines / Q000737:chemistry*; D013237:Stereoisomerism; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry
D010880:Piperidines; D054837:Quinolizidines; D017026:Swainsonine