A divergent approach to 3-piperidinols: a concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton.

Glenn Archibald, Chih-Pei Lin, Peter Boyd, David Barker, Vittorio Caprio

School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, New Zealand.

The Journal of organic chemistry 2012 Sep 21

filter terms:

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.

Citation

Glenn Archibald, Chih-Pei Lin, Peter Boyd, David Barker, Vittorio Caprio. A divergent approach to 3-piperidinols: a concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton. The Journal of organic chemistry. 2012 Sep 21;77(18):7968-80