5-exo Radical cyclization onto 3-alkoxyketimino-1, 6-anhydromannopyranoses. Efficient preparation of synthetic intermediates for (-)-tetrodotoxin.
Ketoxime ethers at C3 of 1,6-anhydro-beta-D-mannopyranose derivatives were found to be useful 5-exo radical traps of alkyl and vinyl radicals generated at a chain tethered to the C2 hydroxyl group, allowing advanced synthetic intermediates for (-)-tetrodotoxin to be prepared from D-mannose in good overall yield.
Noya
B
B
Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15706 Santiago de Compostela, Spain.
Paredes
M D
MD
Ozores
L
L
Alonso
R
R
D000478:Alkylation; D003500:Cyclization; D008358:Mannose / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008968:Molecular Conformation; D009025:Morpholines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013779:Tetrodotoxin / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry
D009025:Morpholines; D014753:Vinyl Compounds; D013779:Tetrodotoxin; D008358:Mannose