title: Synthesis of Natural and Unnatural Cyclooligomeric Depsipeptides Enabled by Flow Chemistry.
abstract: Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin (1 a), bassianolide (2 b) and enniatin C (1 b). A reliable flow chemistry protocol was established for the coupling and macrocyclisation to form challenging N-methylated amides. This flexible approach has allowed the rapid synthesis of both natural and unnatural depsipeptides in high yields, enabling further exploration of their promising biological activity.
authors: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors: Daniel
authors: D
authors: Lücke
authors: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors: Toryn
authors: T
authors: Dalton
authors: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors: Steven V
authors: http://orcid.org/0000-0002-7816-0042
authors: SV
authors: Ley
authors: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK. zw261@cam.ac.uk.
authors: Zoe E
authors: http://orcid.org/0000-0003-4606-9831
authors: ZE
authors: Wilson
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D001688:Biological Products; D047630:Depsipeptides; D010456:Peptides, Cyclic; C100264:enniatins; C004456:beauvericin; C035050:bassianolide
keywords: cyclooligomeric depsipeptides; flow chemistry; macrocycles; natural products; peptides