title: Enantioselective synthesis of lepadins A-D from a phenylglycinol-derived hydroquinolone lactam.
abstract: The marine alkaloids (-)-lepadins A-C and (+)-lepadin D, belonging to two diastereoisomeric series, were synthesized from an (R)-phenylglycinol-derived tricyclic lactam via a common cis-decahydroquinoline intermediate. Crucial aspects of the synthesis are the stereochemical control in the assembly of the cis-decahydroquinoline platform, in the introduction of the C2 methyl and C3 hydroxy substituents, and in the generation of the C5 stereocenter.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona (Spain), Fax: (+34) 93-402-45-39 http://www.ub.edu/sintefarma/. amat@ub.edu.
authors.forename: Mercedes
authors.initials: M
authors.lastname: Amat
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona (Spain), Fax: (+34) 93-402-45-39 http://www.ub.edu/sintefarma/
authors.forename: Alexandre
authors.initials: A
authors.lastname: Pinto
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona (Spain), Fax: (+34) 93-402-45-39 http://www.ub.edu/sintefarma/
authors.forename: Rosa
authors.initials: R
authors.lastname: Griera
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona (Spain), Fax: (+34) 93-402-45-39 http://www.ub.edu/sintefarma/. joanbosch@ub.edu.
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D004983:Ethanolamines / Q000737:chemistry*; D005998:Glycine / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D004983:Ethanolamines; D006571:Heterocyclic Compounds; D007769:Lactams; D011804:Quinolines; C461204:decahydro-3-hydroxy-5-(5'-hydroxyoctyl)-2-methylquinoline; C432305:lepadin A; C414923:lepadin B; C442360:lepadin C; C005332:N-phenylethanolamine; C037920:decahydroquinoline-5-carboxylic acid; D005998:Glycine
keywords: alkaloids; asymmetric synthesis; lactams; nitrogen heterocycles; total synthesis