%0 Journal Article
%T Palladium-catalyzed double cross-coupling of E-vinylic dibromides with PhZnCl and the synthesis of tamoxifen
%A Pilli
%A Ronaldo A.
%A Robello
%A Lu¨ªs Gustavo
%J Journal of the Brazilian Chemical Society
%D 2004
%I Sociedade Brasileira de Qu¨ªmica, SBQ
%R 10.1590/S0103-50532004000600023
%X (e)-1,2-vinylic dibromides 11a-f were stereoselectively prepared via bromination of acetylenic compounds with pyridinium tribromide in meoh/ccl4 at low temperature and double cross-coupled with phzncl under pd(0) catalysis (negishi protocol) to afford tri- and tetrasubstituted olefins 14a-e. tamoxifen, a selective estrogen receptor modulator clinically prescribed in breast cancer therapy, was prepared in 7 steps and 30% overall yield from 4-iodophenol (3) as a 2.3:1 mixture of (z)- and (e)-isomers.
%K (e)-1
%K 2-vinylic dibromides
%K double cross-coupling
%K palladium catalysis
%K tri- and tetrasubstituted olefins
%K tamoxifen.
%U http://www.scielo.br/scielo.php?script=sci_abstract&pid=S0103-50532004000600023&lng=en&nrm=iso&tlng=en