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  • Title: A scalable route to trisubstituted (E)-vinyl bromides.
    Author: Cho CG, Kim WS, Smith AB.
    Journal: Org Lett; 2005 Aug 04; 7(16):3569-72. PubMed ID: 16048344.
    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]
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