Iminium Ion Cascade Reactions: Stereoselective Synthesis of Quinolizidines and Indolizidines.

ABSTRACT: A novel iminium ion cascade reaction has been developed that allows for the stereoselective synthesis of a variety of substituted aza-fused bicycles. The combination of amino allylsilanes and aldehydes (or ketones) was used to synthesize a number of quinolizidines and indolizidines in an one-pot reaction sequence. This technology has been used to effect the facile syntheses of several indolizidine and quinolizidine natural products including, (±)-epilupinine, (±)-tashiromine, and (-)-epimyrtine. Substrate scope has been examined varying the type of amino allylsilanes (primary, secondary and conjugated) and carbonyl compounds (aldehydes and ketones) to give a variety of fused ring structures. Varying the components chosen allows for the inclusion of synthetically useful functional groups at

SUBMITTER: Amorde SM 

PROVIDER: S-EPMC2947323 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature