A general synthetic route to enantiopure 5-substituted cis-decahydroquinolines.
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.
Amat
Mercedes
M
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
Fabregat
Robert
R
Griera
Rosa
R
Bosch
Joan
J
D007769:Lactams / Q000737:chemistry; D010084:Oxidation-Reduction; D011422:Propionates / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D007769:Lactams; D011422:Propionates; D011804:Quinolines; C037920:decahydroquinoline-5-carboxylic acid