Syntheses of hybrid cyclopeptidyl [n]sulfanes by internal alkyl group exchange

Abstract

Internal capture of the cinnamyl carbocation by tert-butylated cysteine derivatives within composite peptides affords macrocycles. The reactions proceed rapidly at room temperature and allow syntheses of mono, di and trisulfide containing ring systems. The methodology provides facile access to peptidomimetic sulfanes of varying ring size, sulfur content and constitution under non-oxidative conditions.