Rapid construction of substituted 3-amino-1, 5-benzothiazepin-4(5H)-one dipeptide scaffolds through an Ugi-4CR – Ullmann cross-coupling sequence. Issue 8 (30th January 2018)

• Record Type: Journal Article
• Authors: Van der Poorten, O.; Van Den Hauwe, R.; Hollanders, K.; Maes, B. U. W.; Tourwé, D.; Jida, M.; Ballet, S.
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 8(2018)
• Page Start: 1242
• Page End: 1246
• Publication Date: 2018-01-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob03094k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A 3-step methodology afforded the title compounds in moderate to good yields, with in silico and NMR conformational studies showing that the lowest energy conformers stabilize γ- and β-turn structures. Abstract : A 3-step methodology for the synthesis of 1, 5-benzothiazepin-4(5 H )-one dipeptidomimetics has been elaborated via an Ugi-4CR followed by a S -trityl deprotection and an intramolecular Cu(i )-catalyzed Ullmann condensation with moderate to good yields. In silico and NMR conformational studies showed that the lowest energy conformers stabilize γ- and β-turn structures.