A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton

作者：Archibald Glenn; Lin Chih Pei; Boyd Peter; Barker David^*; Caprio Vittorio

来源：Journal of Organic Chemistry, 2012, 77(18): 7968-7980.

DOI：10.1021/jo3011914

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.

• 出版日期2012-9-21