EMAIL THIS PAGE TO A FRIEND

Organic letters

A scalable route to trisubstituted (E)-vinyl bromides.


PMID 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]

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

V1902
Vinyl bromide, 98%
C2H3Br
434191
Vinyl bromide solution, 1.0 M in THF
C2H3Br