title: Stereoselective synthesis of β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones.
abstract: Zinc or a chromium(II) source with 3-(bromomethyl)furan-2(5H)-one (3) and an aldehyde gives β-(hydroxymethylaryl/alkyl)-α-methylene-γ-butyrolactones 5 in good yields and high diastereoselectivities. The methodology is demonstrated in concise syntheses of (±)-hydroxymatairesinol (8) and (±)-methylenolactocin (10) by subsequent arylboronate conjugate addition and translactonization, respectively.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Oxford, UK. david.hodgson@chem.ox.ac.uk
authors.forename: David M
authors.initials: DM
authors.lastname: Hodgson
authors.forename: Eric P A
authors.initials: EP
authors.lastname: Talbot
authors.forename: Barry P
authors.initials: BP
authors.lastname: Clark
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002857:Chromium / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D005663:Furans; D007783:Lactones; D017705:Lignans; C419306:hydroxymatairesinol; D002857:Chromium; C056801:methylenolactocin; C014096:alpha-methylene gamma-butyrolactone; D015032:Zinc; D015107:4-Butyrolactone