A scalable route to trisubstituted (E)-vinyl bromides

Cheon Gyu Cho, Won Suk Kim, Amos B. Smith

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)3569-3572
Number of pages4
JournalOrganic Letters
Volume7
Issue number16
DOIs
StatePublished - 4 Aug 2005

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