Late-stage diversification of peptidomimetics and oligopeptides via gold-catalyzed post-Ugi cyclization

A chemo-and regioselective gold-catalyzed tandem 6-endo-dig cyclization/enyne cycloisomerization/1,2migration process for the synthesis of decorated peptidomimetics is developed. Various migrating groups such as aryl, heteroaryl and alkyl are tolerated in this method under mild conditions. This protocol is successfully utilized to modify various oligopeptides, including substrates bearing the drug amantadine, in a rapid and step economical manner through the combination with the Ugi reaction.

Automated summary

A chemo- and regioselective gold-catalyzed tandem reaction has been developed for the synthesis of decorated peptidomimetics. This mild condition method tolerates various migrating groups, such as aryl, heteroaryl, and alkyl. The protocol has been successfully applied to modify various oligopeptides, including those bearing the drug amantadine, in a rapid and economical manner through the combination with the Ugi reaction.