title: cis-Decahydroquinolines via asymmetric organocatalysis: application to the total synthesis of lycoposerramine Z.
abstract: A concise synthesis of the Lycopodium alkaloid lycoposerramine Z is reported. Key to the strategy is a one-pot organocatalyzed Michael reaction followed by a domino Robinson annulation/intramolecular aza-Michael reaction promoted by LiOH, leading to enantiopure cis-decahydroquinolines.
authors.affiliation: Laboratori de Química Orgánica, Facultat de Farmàcia, IBUB, Universitat de Barcelona, Av. Joan XXIII, s/n, 08028 Barcelona, Spain. benbradshaw@ub.edu
authors.forename: Ben
authors.initials: B
authors.lastname: Bradshaw
authors.forename: Carlos
authors.initials: C
authors.lastname: Luque-Corredera
authors.forename: Josep
authors.initials: J
authors.lastname: Bonjoch
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D003497:Cyclic N-Oxides; D011804:Quinolines; C546489:lycoposerramine-Z; C037920:decahydroquinoline-5-carboxylic acid