C. Cho, Won‐Suk Kim, Amos B. Smith
Jul 15, 2005
Citations
0
Influential Citations
15
Citations
Journal
Organic letters
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]