Asymmetric Synthesis. 2. Practical Method for the Asymmetric Synthesis of Indolizidine Alkaloids: Total Synthesis of (-)-Monomorine I

Article abstract of DOI:10.1021/jo00205a023

The alkylation of the chiral 2-cyano-6-oxazolopiperidine synthon (1) with the iodo ketal 2 gave, after selective cleavage of the cyano group, the oxazolopiperidine 4 having the 2S configuration.Compound 4 was alkylated with CH3MgI, giving a 4:1 mixture of