A total synthesis of the quinolizidine alkaloid (+)-epiquinamide 1 has been achieved starting from ()-pipecolinic acid 3. The key step is the highly diastereoselective addition of a TBDMS-protected propargyl alcohol to a chiral aldehyde derived from 3 to give erythro alkynol 19, which is then easily transformed into the desired bicyclic skeleton.
