title: Synthesis of peptidomimetics, δ- and ε-lactam tetrazoles.
abstract: A concise two-step procedure for the synthesis of novel δ-lactam tetrazoles has been established via the Ugi-azide reaction using 5-oxohexanoic acid along with primary amines, isocyanides, and azidotrimethylsilane followed by 1,1'-carbonyldiimidazole-mediated intramolecular amide formation. Expansion to ε-lactam tetrazole scaffolds was accomplished using methyl 6-oxoheptanoate via the same Ugi-azide reaction followed by basic hydrolysis and SOCl(2) activation to enable lactam formation.
authors.affiliation: BIO5 Oro Valley, The University of Arizona, Oro Valley, AZ 85737, USA.
authors.forename: Steven
authors.initials: S
authors.lastname: Gunawan
authors.forename: Kristen
authors.initials: K
authors.lastname: Keck
authors.forename: Alex
authors.initials: A
authors.lastname: Laetsch
authors.forename: Christopher
authors.initials: C
authors.lastname: Hulme
mesh_terms: D060326:Chemistry Techniques, Synthetic; D045786:Diterpenes, Kaurane / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D057786:Peptidomimetics / Q000138:chemical synthesis* / Q000737:chemistry*; D013777:Tetrazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C516048:5-oxokaurenoic acid; D045786:Diterpenes, Kaurane; D007769:Lactams; D057786:Peptidomimetics; D013777:Tetrazoles