title: Enantio- and diastereoconvergent cyclocondensation reactions: synthesis of enantiopure cis-decahydroquinolines.
abstract: Up to four stereocenters with a well-defined configuration are generated in a single synthetic step by the cyclocondensation of (R)-phenylglycinol or (1S,2R)-1-amino-2-indanol with stereoisomeric mixtures (racemates, meso forms, diastereoisomers) of cyclohexanone-based δ-keto-acid and δ-keto-diacid derivatives in enantio- and diastereoconvergent processes that involve dynamic kinetic resolution and/or desymmetrization of enantiotopic groups. A detailed analysis of the stereochemical outcome of this process is presented. This method provides easy access to enantiopure 8- and 6,8-substituted cis-decahydroquinolines, including alkaloids of the myrioxazine family.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona (Spain). amat@ub.edu.
authors.forename: Mercedes
authors.initials: M
authors.lastname: Amat
authors.forename: Elena
authors.initials: E
authors.lastname: Ghirardi
authors.forename: Laura
authors.initials: L
authors.lastname: Navío
authors.forename: Rosa
authors.initials: R
authors.lastname: Griera
authors.forename: Núria
authors.initials: N
authors.lastname: Llor
authors.forename: Elies
authors.initials: E
authors.lastname: Molins
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D003500:Cyclization; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000605:Amino Alcohols; D011804:Quinolines; C037920:decahydroquinoline-5-carboxylic acid
keywords: alkaloids; asymmetric synthesis; diastereoselectivity; lactams; nitrogen heterocycles