title: A Lanthanide(III) Triflate Mediated Macrolactonization/Solid-Phase Synthesis Approach for Depsipeptide Synthesis.
abstract: The effect of dysprosium(III) triflate on macrolactonization reactions to form depsipeptides using MNBA (Shiina's reagent) is reported. Improved yields were obtained for the formation of 16-membered depsipeptides using lanthanide triflate additives. The use of a macrocyclization strategy permits the use of a semiautomated solid-phase synthesis approach for the rapid synthesis of analogues of the antibacterial A54556 acyldepsipeptides in only two physical operations, requiring only final product purification after cyclization.
authors: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON Canada, M5S 3H6.
authors: Jordan D
authors: JD
authors: Goodreid
authors: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON Canada, M5S 3H6.
authors: Eduardo da Silveira
authors: Eda S
authors: dos Santos
authors: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON Canada, M5S 3H6.
authors: Robert A
authors: RA
authors: Batey
mesh_terms: D000900:Anti-Bacterial Agents; D003500:Cyclization; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis; D028581:Lanthanoid Series Elements / Q000737:chemistry*; D015394:Molecular Structure; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000900:Anti-Bacterial Agents; D047630:Depsipeptides; D007783:Lactones; D028581:Lanthanoid Series Elements