Synthesis Of Indolizidines Research Articles

Indolizidine synthesis by transannular cyclization

AbstractBeckmann rearrangement of alkylcyclooctenone oximes VIa and VIb gave corresponding nine‐membered lactams 1,3,4,5,8,9‐hexahydro‐3‐methyl‐2H‐azonin‐2‐one (VIIIa) and 1,3,4,5,8,9‐hexahydro‐3‐butyl‐2H‐azonin‐2‐one (VIIIb), respectively. A stereospecific transannular cyclization was induced by mercuric acetate leading to alkyl indolizinones Xa and Xb. Temperature and solvent dependent nmr spectra of the medium ring lactams indicates the stereochemical control is caused by steric interactions of the alkyl side chain. Lithium aluminum hydride reduced Xa/Xb to cis‐octahydro‐6‐methylindolizidine (XIa) and cis‐octahydro‐3‐n‐butylindolizidine (XIb).