title: Biomimetic construction of the hydroquinoline ring system. Diastereodivergent enantioselective synthesis of 2,5-disubstituted cis-decahydroquinolines.
abstract: 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.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine, University of Barcelona, 08028 Barcelona,Spain. amat@ub.edu
authors.forename: Mercedes
authors.initials: M
authors.lastname: Amat
authors.forename: Robert
authors.initials: R
authors.lastname: Fabregat
authors.forename: Rosa
authors.initials: R
authors.lastname: Griera
authors.forename: Pedro
authors.initials: P
authors.lastname: Florindo
authors.forename: Elies
authors.initials: E
authors.lastname: Molins
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D032701:Biomimetics / Q000379:methods*; D018716:Molecular Mimicry; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011804:Quinolines