A. Mollica, A. Stefanucci, Roberto Costante
May 18, 2011
Citations
0
Influential Citations
21
Citations
Journal
Planta Medica
Abstract
Abstract 5,6-Dibromo-tryptophan is an interesting amino acid whose derivatives and analogues are found in a variety of highly bioactive natural compounds. Notwithstanding its relevance no data concerning this compound are found in the literature. Here an efficient pathway for the synthesis of 5,6-dibromo-tryptophan derivatives is reported. The reaction is performed by using 6-Br-isatin as starting material. Selective bromination at position 5 was followed by BH 3 reduction of the intermediate α-keto-amide and alkylation with Ser-OH in Ac 2 O/AcOH. Optical resolution was effected by enzymatic de-acetylation of the obtained racemic mixture. Finally, in situ N α -Boc protection of the optically pure S form yielded the desired N α -Boc-( S )-5,6-dibromo-tryptophan.