title: Access to enantiopure 4-substituted 1,5-aminoalcohols from phenylglycinol-derived δ-lactams: synthesis of Haliclona alkaloids.
abstract: LiNH2BH3-promoted reductive opening of 8-substituted phenylglycinol-derived oxazolopiperidone lactams leads to enantiopure 4-substituted-5-aminopentanols, which are used as starting building blocks in the synthesis of the Haliclona alkaloids haliclorensin C, haliclorensin, and halitulin (formal). The starting lactams are easily accessible by a cyclocondensation reaction of (R)-phenylglycinol with racemic γ-subtituted δ-oxoesters, in a process that involves a dynamic kinetic resolution.
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
authors.forename: Guillaume
authors.initials: G
authors.lastname: Guignard
authors.forename: Núria
authors.initials: N
authors.lastname: Llor
authors.forename: Joan
authors.initials: J
authors.lastname: Bosch
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry*; D000818:Animals; D004983:Ethanolamines / Q000737:chemistry*; D047129:Haliclona / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000605:Amino Alcohols; D004983:Ethanolamines; D006576:Heterocyclic Compounds, 4 or More Rings; D007769:Lactams; C484766:haliclorensin; C548932:haliclorensin C; C484764:halitulin; C005332:N-phenylethanolamine