Total synthesis of everninomicin 13,384-1--Part 2: synthesis of the FGHA2 fragment.
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.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA. kcn@scripps.edu
Mitchell
H J
HJ
Fylaktakidou
K C
KC
Rodríguez
R M
RM
Suzuki
H
H
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013057:Spectrum Analysis
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; C001202:evernimicin