title: Enantioselective Total Synthesis of Fluvirucinin B1.
abstract: A convergent synthesis of fluvirucinin B1 from acid ent-6a and nitrile ent-9, involving an organocopper coupling, a stereoselective allylation, a ring-closing metathesis reaction, and a stereoselective hydrogenation as the key steps, is reported. The starting building blocks have been prepared in a straightforward manner from a common phenylglycinol-derived lactam 1. An unprecedented regioselective oxidation of phenylglycinol-derived secondary amines 5 to carboxylic acids 6 has been developed.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 08028 Barcelona, Spain.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Guignard
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 08028 Barcelona, Spain.
authors.forename: Núria
authors.initials: N
authors.lastname: Llor
authors.affiliation: Institut de Ciència de Materials (CSIC) , Campus UAB, 08193 Cerdanyola, Spain.
authors.forename: Elies
authors.initials: E
authors.lastname: Molins
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 08028 Barcelona, Spain.
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona , 08028 Barcelona, Spain.
authors.forename: Mercedes
authors.initials: M
authors.lastname: Amat
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004983:Ethanolamines / Q000737:chemistry*; D006865:Hydrogenation; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D004983:Ethanolamines; D007769:Lactams; C000588927:fluvirucin B1; C005332:N-phenylethanolamine