title: Novel synthesis of carbohydrate fused α-amino γ-lactams and glycopeptides by NIS mediated ring opening of donor-acceptor substituted cyclopropanes.
abstract: α-Amino γ-lactams have been synthesized from carbohydrate derived cyclopropanecarboxylates using N-iodosuccinimide (NIS) and NaN3. Cyclopropane ring opening with NIS and NaN3 in different solvents has been studied. Reductive cyclization of the intermediate di-azides leads to the carbohydrate fused α-amino γ-lactam and γ-lactams. Additionally, the methodology has been successfully extended to the synthesis of a glycopeptide.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
authors.forename: Gade
authors.initials: G
authors.lastname: Kishore
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
authors.forename: Vibha
authors.initials: V
authors.lastname: Gautam
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India. Electronic address: scn@orgchem.iisc.ernet.in.
authors.forename: Srinivasan
authors.initials: S
authors.lastname: Chandrasekaran
mesh_terms: D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis*; D007769:Lactams / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D019810:Sodium Azide / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry*
chemical_list: D003521:Cyclopropanes; D006020:Glycopeptides; D007769:Lactams; D013388:Succinimides; C008155:N-iodosuccinimide; D019810:Sodium Azide
keywords: Donor–acceptor cyclopropane; Glycopeptide; N-Iodosuccinimide; Reductive cyclization; Ring opening; γ-Lactam