title: Asymmetric total syntheses of (-)-variabilin and (-)-glycinol.
abstract: Total syntheses of (-)-variabilin and (-)-glycinol have been accomplished, using the catalytic, asymmetric "interrupted" Feist-Bénary reaction (IFB) as the key transformation to introduce both stereogenic centers. A monoquinidine pyrimidinyl ether catalyst affords the IFB products in over 90% ee in both cases. Other key steps include an intramolecular Buchwald-Hartwig coupling and a nickel-catalyzed aryl tosylate reduction.
authors.affiliation: Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459, USA. mcalter@wesleyan.edu
authors.forename: Michael A
authors.initials: MA
authors.lastname: Calter
authors.forename: Na
authors.initials: N
authors.lastname: Li
mesh_terms: D002384:Catalysis; D044948:Flavonols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D011506:Proteins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D044948:Flavonols; D011506:Proteins; C100625:variabilin; D009532:Nickel; C540862:glycinol