Biomimetic construction of the hydroquinoline ring system. Diastereodivergent enantioselective synthesis of 2,5-disubstituted cis-decahydroquinolines.
The straightforward enantioselective construction of the hydroquinoline ring system from 1,5-polycarbonyl derivatives, using (R)-phenyglycinol as a chiral latent form of ammonia, is reported. The process mimics the key steps believed to occur in nature in the biosynthesis of amphibian decahydroquinoline alkaloids. Diastereodivergent routes to enantiopure cis-2,5-disubstituted decahydroquinolines, including the alkaloid pumiliotoxin C (cis-195A), are developed.
Amat
Mercedes
M
Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine, University of Barcelona, 08028 Barcelona,Spain. amat@ub.edu
Fabregat
Robert
R
Griera
Rosa
R
Florindo
Pedro
P
Molins
Elies
E
Bosch
Joan
J
D032701:Biomimetics / Q000379:methods*; D018716:Molecular Mimicry; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011804:Quinolines