A practical synthetic route to enantiopure 5-substituted cis-decahydroquinolines has been developed, the key steps being a stereoselective cyclocondensation of 2-substituted 6-oxocyclohexenepropionates 2 with (R)-phenylglycinol, the stereoselective hydrogenation of the resulting unsaturated tricyclic lactams, and the stereoselective reductive cleavage of the oxazolidine ring.
Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain. amat@ub.edu
