title: Stereoselective synthesis of (-)-lepadins A-C.
abstract: A concise synthesis of the marine alkaloids (-)-lepadins A-C from a phenylglycinol-derived tricyclic lactam is reported. Key steps from the stereochemical standpoint involve stereoselective cyclocondensation, double bond hydrogenation, oxazolidine opening, hydroboration-oxidation, and Horner-Wadsworth-Emmons reactions.
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: Alexandre
authors.initials: A
authors.lastname: Pinto
authors.forename: Rosa
authors.initials: R
authors.lastname: Griera
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000470:Alkaloids; D011804:Quinolines; C432305:lepadin A; C414923:lepadin B; C442360:lepadin C