title: A scalable route to trisubstituted (E)-vinyl bromides.
abstract: An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of alpha,beta-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(11) moieties of (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), illustrate the utility of this protocol. [reaction: see text]
authors.affiliation: Department of Chemistry, Hanyang University, Seoul, Korea 133-791. ccho@hanyang.ac.kr
authors.forename: Cheon-Gyu
authors.initials: CG
authors.lastname: Cho
authors.forename: Won-Suk
authors.initials: WS
authors.lastname: Kim
authors.forename: Amos B
authors.initials: AB
authors.lastname: Smith
mesh_terms: D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis*
chemical_list: D006842:Hydrocarbons, Brominated; D007783:Lactones; D014753:Vinyl Compounds; C003763:vinyl bromide