Novel Chiral Synthetic Path to Indolizidine and Quinolizidine Alkaloids by Means of a Samarium Diiodide-Promoted Reductive Carbon-Nitrogen Cleavage Reaction: Synthesis of (+)-(8R, 8aR)-Perhydro-8-indolizidinol and (—)-Deoxynupharidine

Abstract

Novel chiral synthetic procedures for indolizidine and quinolizidine alkaloids were developed, where a samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was employed as a key step. Application of the procedure led to the total synthesis of (+)-(8R, 8aR)-perhydro-8-indolizidinol and (-)-deoxynupharidine.