A scalable route to trisubstituted (E)-vinyl bromides.
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]
Cho
Cheon-Gyu
CG
Department of Chemistry, Hanyang University, Seoul, Korea 133-791. ccho@hanyang.ac.kr
Kim
Won-Suk
WS
Smith
Amos B
AB
D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D006842:Hydrocarbons, Brominated; D007783:Lactones; D014753:Vinyl Compounds; C003763:vinyl bromide