title: Total synthesis of thiopeptide antibiotics GE2270A, GE2270T, and GE2270C1.
abstract: The total syntheses of the thiopeptide antibiotics GE2270A (7), GE2270T (8), and GE2270C1 (9) are described. The original synthetic strategies employed utilized the hetero-Diels-Alder reaction to construct the pyridine core of the target molecules and relied on a macrolactamization process to construct the macrocycle. The hetero-Diels-Alder-based strategy finally evolved allows the introduction of all four thiazole units attached to the pyridine ring and a one-pot sequence for macrocyclization and side-chain extension, culminating in highly convergent and expedient syntheses of these molecules as exemplified by a 24-step synthesis of GE2270C1 (9).
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. kcn@scripps.edu
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: Dattatraya H
authors.initials: DH
authors.lastname: Dethe
authors.forename: Gulice Y C
authors.initials: GY
authors.lastname: Leung
authors.forename: Bin
authors.initials: B
authors.lastname: Zou
authors.forename: David Y-K
authors.initials: DY
authors.lastname: Chen
mesh_terms: D000081:Acetamides / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001393:Azoles / Q000737:chemistry; D006900:Hydroxylation; D018942:Macrolides / Q000737:chemistry; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D010649:Phenylalanine / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000081:Acetamides; D000900:Anti-Bacterial Agents; D001393:Azoles; C526942:GE2270C1; C520601:GE2270T; D018942:Macrolides; D010456:Peptides, Cyclic; D011725:Pyridines; D013438:Sulfhydryl Compounds; D013844:Thiazoles; D010649:Phenylalanine; C030686:acetamide; C068122:GE 2270 A; C023666:pyridine