A Scalable Route to Trisubstituted (<i>E</i>)-Vinyl Bromides

Abstract

An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of α,β-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