title: Total synthesis of everninomicin 13,384-1--Part 2: synthesis of the FGHA2 fragment.
abstract: The stereoselective synthesis of everninomicin's 13,384-1 (1) FGHA2 fragment (2) in a suitable form for incorporation into the final target (1) is described. The construction of the FG 1,1'-disaccharide linkage relied on a new method based on tin-acetal chemistry, while for the GH orthoester bridge, a number of approaches were explored. Final success for the latter construction came when a novel 1,2-phenylseleno migration reaction was applied to couple rings G and H, followed by ketene acetal and orthoester formation.
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA. kcn@scripps.edu
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: H J
authors.initials: HJ
authors.lastname: Mitchell
authors.forename: K C
authors.initials: KC
authors.lastname: Fylaktakidou
authors.forename: R M
authors.initials: RM
authors.lastname: Rodríguez
authors.forename: H
authors.initials: H
authors.lastname: Suzuki
mesh_terms: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013057:Spectrum Analysis
chemical_list: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; C001202:evernimicin