%0 Journal Article
%T Synthesis of Benzomacrolactam by 11£¿endo Selective Aryl Radical Cyclization of 2£¿Iodobenzamide Derived from D£¿Galactose
%A Binatti
%A Ildefonso
%A Prado
%A Maria Auxiliad£¿ra F.
%A Alves
%A Ricardo J.
%A Souza Filho
%A Jos¨¦ D.
%J Journal of the Brazilian Chemical Society
%D 2002
%I Sociedade Brasileira de Qu¨ªmica, SBQ
%R 10.1590/S0103-50532002000500005
%X encouraged by our previous studies of tri-n-butyltin-mediated radical cyclization reaction of o-iodobenzamides, we applied this methodology to the synthesis of benzomacrolactam 2 from methyl 4-o-allyl-2,3-di-o-benzyl-6-deoxy-6-(2-iodobenzoylamino)- ¦Á-d-galactopyranoside 1. apart from the macrolactam 2, resulting from regioselective 11-endo aryl radical cyclization, the hydrogenolysis produt 3 was obtained. the o-iodobenzamide 1 was prepared in eight conventional synthetic steps from methyl ¦Á-d-galactopyranoside. the unequivocal structures of 1, 2 and 3 were supported by 1h, 13c and dept nmr spectroscopy and by cosy and hmqc experiments.
%K benzomacrolactam
%K aryl radical cyclization.
%U http://www.scielo.br/scielo.php?script=sci_abstract&pid=S0103-50532002000500005&lng=en&nrm=iso&tlng=en