A plan is proposed, based on successful preliminary investigation, to reach chiral, enantiomerically pure, biologically active compounds or key precursors to these materials. By use of chiral bicyclic lactams, prepared from Gamma- or Delta-ketoacids or aldehyde acids and (S)-valinol, we hope to introduce, in an enantioselective manner, a variety of substituents to form a chiral quaternary center. This methodology will be used to prepare optically active precursors to the Amaryllidaceae, Aspidosperma, and Erythrina alkaloids, insect pheromones (Grandisol, Anistrephin), and octalones for steroid synthesis. In addition a number of useful compounds containing chirality due to the quaternary center will be prepared.
| Resek, James E (2008) Intramolecular ene reaction of a chiral bicyclic lactam. J Org Chem 73:9792-4 |
