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

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.