Journal of Organic Chemistry p. 1821 - 1829 (1986)
Update date:2022-08-03
Topics:
Kemp, D. S.
Galakatos, Nicholas George
Peptide bond formation by intramolecular acyl transfer across a rigid template is outlined.The template precursor 6-hydroxy-4-mercaptodibenzofuran (3) is obtained from 4-methoxydibenzofuran by metalation with n-butyllithium, oxidation with elemental sulfur, and demethylation.Routes to 4-(acyloxy)-6-mercaptodibenzofurans 4 are reported.Esters 4 derived from simple urethane N-blocked α-amino acids are conveniently prepared by direct acylation of 6-hydroxy-4-(methoxycarbonyldithio)dibenzofuran (12), followed by reduction with tri-n-butylphosphine.Esters 4 derived from the C-terminal carboxyl groups of peptides are prepared by a novel variant of conventional solid-phase peptide synthesis in which the chain elongation steps are carried out on the 4-((α-aminoacyl)oxy)-6-dibenzo-furanyldithio function linked through the disulfide to a polymeric support.At the completion of the elongation steps, release of 4 from the resin is achieved by reduction of the disulfide bond with tri-n-butylphosphine.
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